Tutoring Has Its Rewards
- 4 years ago
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Tutoring Has Unexpected Rewards free porn video
My sister Kate and I were seventeen, twins, and in our junior year of high school. That's where our similarities ended. She was popular, athletic, outgoing, and had lots of friends. I was her polar opposite: nerdy, socially awkward, only a handful of friends. Pretty much irrelevant in our school's world. The only thing I knew I had going for me right from day one of high school was my brain. I was smart. Really smart. Top-of-the-class smart.
But as high school dragged on, I found I had something else going for me. Turned out genetics were kind to me. Simply using the eye test in the locker room after gym class made it plainly evident. I had a large penis, something to at least be proud of, even if no girl in the school would ever find out. Guys where I stood in the social pecking order never got the girl. Or so I thought.
Just after the holiday break of our junior year, I was fast on my way to another perfect school year. Attend every day--check. Have straight A's--check. My sister was also very smart but didn't really apply herself like I did. She was busy being a dual-sport athlete. Being a girlfriend. Being Miss Popular.
Kate's best friend, Ashley also played sports and was extremely popular, especially with the boys. She had acquired a reputation for being fairly easy for the guys to have fun with. It was rather apparent why. Ashley was as beautiful a girl as you'd ever see: soft shiny shoulder-length hair, flawless radiant skin, luscious lips, supple breasts that always seemed to fill out whatever she wore perfectly, legs that went on for days, and a tight butt that swayed just right with every step. She was my nighttime muse, if you know what I mean.
One afternoon after school I was in my room doing my homework when Kate knocked on my door. I told her she could come in and to my surprise, she had Ashley with her. Ashley was actually in my room, and she had a look of disdain on her face. It was also carrying a look of embarrassment.
"Hey, bro," Kate began. "Do you think we can talk with you for a minute?"
As they both filed into my room, Kate pleaded, "Well, we need you to promise not to say anything about this conversation to anyone."
"Kate, you see who I talk to at school. Who am I possibly going to say anything to?" I deadpanned.
"Okay, here's the thing," she started only to be interrupted by Ashley.
"We're serious, Kyle. No one can know about this," she implored.
"Ï get it. You don't have to worry about me saying anything to anyone. You have my word. But this must be really bad if you need to be this secretive," I reassured.
"So the thing is, Ky," Ashley began. "I'm not doing well in some of my classes. Like, it's terrible."
"Well, that's not that bad, Ash," I retorted. "Why so secretive about that? I mean, no offence, but C's still get the job done."
"No, Kyle," she sulked. "It's worse than that. I'm failing two classes." A tear ran down her cheek. "My teachers said if I don't get back to a passing grade then I'll be held back. I'd be a joke in school." Ashley spoke quiveringly as she tried in vain to choke back tears.
"So I made a suggestion, Kyle," Kate interjected. "You're the smartest person either of us knows, and since word can't get out no one would be suspicious if she was hanging out here since everyone knows Ash and I are BFFs. "
"If I didn't know any better, I'd think you're asking me to be her tutor," I said looking at Kate.
"That's exactly what I'm asking, Ky," she shot back.
"I'll even pay you, Kyle. I'm desperate here. I have no one else to turn to," Ashley said emotionally.
"Well, your money is no good here, Ash," I replied. "Kate would kill me if I took any compensation from you. But before I agree to help you, there are some rules to this."
"Whatever, yes. I'll do anything you want, just please help me," Ashley pleaded.
"Relax," I said reassuringly. "First, I won't do the work for you. Second, when you're here for tutoring, you're here for tutoring. That means not hanging with Kate, not on the phone, not anything but the work. Third, you'll have to really apply yourself. You can't expect things to improve overnight. This will be tough, but if you put the work in and trust me, then we'll get this. Okay, Ash?"
"I get it, Kyle," she affirmed. "Believe me, I understand and I know you'll do what you can to help. I trust you."
"And there's rules for you too, Kate," I said peering in her direction. "If she's here to study you can't be a distraction. No texting her. No barging in to talk or gossip. If things are as bad as you're both saying, then you'll have to let her be, and let me do what I can to help. Understand?"
"Yes sir, aye-aye, Captain," she said, half-heartedly giving me a salute.
"Alright then, I'm in," I replied. "Your first session is day after tomorrow. Bring your books and an open mind. Let's get you to senior year."
Our tutoring sessions got off to a rocky start. I had underestimated how far Ashley was behind. Ashley underestimated how seriously I was going to take being her tutor. In the first two weeks, we were both going to give up on the whole thing at least a half dozen times.
Truth was, I'd never quit on her. Not because I had lofty principles. Fact was, Ashley was one of the hottest girls in the entire school, and guys of my ilk really never would have this kind of chance to be around a girl like her. Sure, I'd stick with it because I knew it meant a lot to Kate, but it was more Ashley's attractiveness that was going to keep me involved.
Once Ashley and I got past the early hiccups, she began to latch onto some things. Her aptitude began to improve and the F's were becoming D's, the D's were moving towards C's. Since she was seeing some improvement Ashley kept up her end of the deal. When she was over to be tutored she really put forth the effort. Kate made sure to give us the time and space we needed to get Ashley in the right place.
By the end of the third of four marking periods, Ashley had gone from F's to a C in the two classes I was helping her in. She was happy. I knew there was still no margin for error. Mess up in the fourth semester or on the final and it was back to junior year, a point I made often to keep Ashley focused and determined to reach her goal.
The fourth semester was another improvement. She secured two more C's. Good, but still no sure thing. If Ashley mailed in the finals and failed them, she'd be staying back in junior year while Kate and I moved on to being seniors. So we needed to bear down.
Ashley was over every night for a week straight. She was really putting in a great effort, far better than I anticipated. Candidly, she admitted it was the hardest she had prepared for school work in her life. I was proud of her trying, and I knew in my heart she'd do alright. She was nervous as she went into school on Thursday to take her two finals. Let the waiting begin.
On Friday, Kate and Ashley had plans to go out with some friends. Ashley came over to meet up with my sister before going out. Wow, did she look great. Tight jeans hugged her toned legs and plump ass just right. A rather low cut and revealing t-shirt framed and accentuated her perky breasts. It was all I could do to keep from staring.
After they left I knew exactly what I'd be doing and who I'd be thinking about while I was doing it.
Kate knocked on my door late Monday afternoon after getting home from school. She told me we needed to talk through my closed door. I told her the door was unlocked and she could come in.
"Hey, Ky, how goes it?" she asked.
"I'm good, just reading. What's up?" I replied.
"I just got off the phone with Ashley. She got her grades for the two finals," she offered.
"Oh, I take it from your tone, it didn't go so well," I retorted. "She really tried, but we knew this was a possibility with where she was when we started."
"Well, Ash said it didn't go how she thought it would turn out," Kate answered.
"Man, that's a shame. I really thought she was picking everything up. I figured she'd be alright," I sympathized.
Kate bounded into the room further and hopped on my bed. "Ky, Ash said it went better!" she exclaimed. "She said she got a B on one and she actually aced the other. You're a miracle worker!"
"I don't know about that," I said. "She deserves all the credit. She really applied herself and put the effort in."
"Ashley thanks you," Kate relayed. "She's not sure how she'll ever repay you. And I thank you too, Bro."
"Hey, it's no big deal," I assured Kate. "Tell her I was happy to help, and I'd do anything for you anyway, Sis."
After Kate left my room, I sat up and thought to myself, 'I sure know how Ashley could thank me' as my penis hardened. Oh well, my thoughts would just have to make do.
Thursday, the last day of school. Finally. Even for a nerd like me, summer vacation is a welcome respite. What made the start of this summer vacation better was that I'd be on my own. Dad was away on a business trip until late Saturday. Mom was taking Kate to see some college campuses through the end of the weekend. The house was mine. Unadulterated freedom. Until there was a knock on the door that changed everything.
In the hopes that whoever was at the door would just go away, I didn't immediately go and answer it. But their persistence wore me down. After close to ten minutes, I figured it must be important.
"Oh, hey, Ashley, what's up?" I answered surprised, swinging the door open.
"What the hell, Kyle!" she demanded. "I was out here banging on the door like a lunatic!"
"Uh, sorry. I was in the bathroom," I quickly fibbed. "Kate isn't here. She and Mom already left for their college visits."
"Yeah, I'm aware, Kyle," Ashley shot back as she squeezed herself past me into the house. "I'm not here to see her anyway. I'm here to see you."
"Oh," I mustered. "Why?"
"You don't like my company?" she replied.
"No, it's not that at all," I stammered. "It's just not something you've ever wanted to do before."
"True, but it's also not common for me to have to thank you for something either," Ashley said.
"Kate already passed on your thanks, Ash," I said. "Besides, I didn't do very much. You put the effort in."
"Don't be so modest, Ky," she countered. "You did a really good job of helping me. I don't think anyone could've helped me like you did. And don't tell anyone this, but you were pretty cool to be around too."
"That's kind of you to say, but you don't have to exaggerate," I meekly replied. "And don't worry--secret's safe."
"I'm not. You're the first guy in a really long time who I've hung around with that didn't try and pick me up or get in my pants," Ashley said matter of factly. "For about a day or two, I thought you might have actually been gay."
"Huh?" I replied surprised. "I'm most certainly not," I emphatically retorted.
"I know, silly," she replied, slightly giggling. "I could tell by the way you were looking at me as we progressed with the tutoring."
"I don't know what you mean," I said in a tone even trying to convince myself. "I was just..."
"Relax. I thought it was cute you were checking me out," she interrupted. "You were a gentleman about it. Which is more than I can say for the rest of your male classmates."
"Well, thanks, I suppose," I answered.
"I will say, though, what I did find rather hot about it was that bulge I would see grow every so often," she coyly and calmly divulged.
"Look, I'm sorry, okay?" I assured her. "I didn't..."
"Didn't what, mean for me to see it?" Ashley interrupted again.
"No, I, I'm just sorry, alright?"
"Look, Ky, I don't really care you got excited around me," she reassured. "I mean, in a way, it's a compliment that you did."
"Really?" I asked. "It doesn't make you mad?"
"Mad? No, not at all. In fact, it was a bit of a turn on," she confessed. "Giving my best friend's brother a hard-on."
I just stood there not sure how to react. I was equal parts shocked, nervous, unsure of myself. Here was Ashley, my sister's BFF, a girl I had crushed over for years, telling me I had turned her on. I was beside myself.
Finally, breaking the tension that had filled the room, Ashley spoke. "You've never been with a girl before, have you, Kyle?"
"It's that obvious, eh?" I shot back.
"Aww, its alright, Ky," Ash said, reaching for my hand, sensing my uneasiness. "What do you say we go up to your room and change that?"
I just stood before Ashley, silent, stunned, mouth desert dry, knees trembling like they'd give out at any second.
"I don't know, Ash...I'm...You're...What about Ka--?" I stammered incoherently as Ashley cut me off.
"Listen, Ky, I want to, and you want to. Don't you?" she quizzed. "And as for Kate, I don't see her around anywhere so that shouldn't be a problem."
Pulling me by the arm Ashley basically dragged me to the stairway. She led the way as we ascended the stairs, my mind a blur. 'What's going on? Is this really going to happen? Why would she want to do this with me? What about her friendship with Kate?' Those and any other questions vanished from my conscious as she began taking her shirt off as we climbed the stairs.
Just as she reached the top of the stairs, she reached behind herself and unclasped her bra, letting it fall to the floor. By the time we got into my room, she turned facing me, revealing her naked breasts. Full, hanging perfectly, plump, ready to be squeezed. Beautiful, glorious spheres on full display. To me!
My cock stirred, thinking with a mind of its own, hardening and straining against my boxer briefs inside my shorts as quick as it took me to utter a "Whoa!" as I stood before her.
Ashley unsnapped her jeans and shimmied out of them. She then turned around, back to me. She began to slide her thong down and bent forward at the hips at the same time. She slightly spread her legs apart as the thong was all the way down, allowing me a view of her pussy for the first time. I simply stood there gawking, waiting to wake up and for this dream to sadly end.
Turning back around, Ashley stepped towards me, reaching out to the hemline of my shirt. "It's not fair, me standing here naked and you still have all your clothes on," she said pulling up and removing my shirt. She then began unfastening my belt and unbuttoning my shorts.
"You won't be needing these anymore," Ashley joked with a glint in her eye, sliding them down until they were piled on the floor. I stood before her clad in just those tented boxer briefs and my nerves.
As she looked down, her mouth parted and her eyes grew big. I thought this was all going to be over right then and there. She'd come to her senses.
But to my surprise, she continued on, moving me towards my bed, then sliding her fingers inside the elastic of my underwear she slid them down as slinked to her knees. Almost simultaneously my cock popped out towards her like it was spring loaded just as she reached the floor. Ashley's mouth went agape as she looked at it.
"Kyle, how big is this thing?" she asked. "I mean, I've never seen one this big before in person."
"I actually have no idea, Ash. I never took the time to figure that out," I replied.
Ashley bounded up off the floor and went to my desk and rummaged around until she found a ruler.
"No time like the present to find out, Ky," she blurted.
Ashley took hold of my cock, the first person other than myself to do so, causing it to twitch. She ran her hand up and down my length a couple times, coming to rest at the tip, lifting it slightly. Her other hand drew the ruler up like a sword. She proceeded to put the ruler along the underside of my penis until she was down to the hilt. Ashley ran a finger along the top of my hardness, letting it drop down along the tip until it was on the ruler. Keeping her finger in place, she brought the ruler away from my dick to see the results.
"Holy shhh...I can't believe it!" she exclaimed. "This says that you're eight and seven-eighths inches!" she squealed.
"I knew I was doing okay for myself just from being in the gym locker room," I said proudly.
"Okay!?" Ashley countered. "You're doing way better than okay for yourself, stud."
Ashley flung the ruler across the room and slunk down to her knees in front of me, her eyes wide, gazing up at me. My eyes were transfixed on her, looking down, seeing my cock pointing out, directly level with her mouth.
My mind was racing, my fists balled at my sides, stomach churning, adrenaline pumping. A devilish smirk appeared on Ashley's face as her face got closer and closer to my cock. Her lips parted and my moment was at hand as my cock slid between her lips entering her mouth.
Her tongue slithered along the underside of my shaft. Looking down I could see her cheeks flexing inward as she sucked my dick deeper into her waiting mouth. Without warning, I was on the brink.
"Uh, Ash...you gotta stop!!" I pleaded. " I'm gonna cum!"
That only gave her encouragement. Her pace increased, as did the depth she was taking my cock towards her throat. She must have sensed when I was going to erupt because she pushed her head forward until her nose was against my trimmed pubes. I could feel my cock in the recesses of her throat. That was my breaking point. With a guttural bark, I was barely able to let Ashley know I was there.
"Ash, I'm cumming!" I exclaimed, my cum blasting from my dick. With each spurt, Ashley would let my cock slide outward until just the tip remained in her mouth. She continued to suck on just the head of my cock while stroking my shaft until I was completely spent.
With a sparkle in her eye and an understanding smile, she let my cock loose from her lips. My legs were weary, and I barely was able to fall back onto my bed. Ashley crawled over to the bed and then climbed up joining me. She nestled into me, our naked bodies skin to skin.
"I'm sorry for being so fast," I conceded. "It was all a little more than I could handle."
"No need to apologize, Kyle," she empathized. "None of you guys last long when it's your first time. Besides, you have plenty of time to make up for it."
I simply looked at her and nodded as it dawned on me we had the rest of the day/night and then all of Friday for me to do just that.
"Well, I hope you can be just as good a tutor to me as I was to you, Ash," I said with a feeling of contentment and a newfound lust and desire.
I thought to myself, 'This could be a fun couple of days.'
Cheryl
- 17.02.2021
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- Teen
