The Cheerleader's Kinks | 2016

After my first lessons, Amy continued to broaden they way I thought about sex over the few months we were together.

Amy enjoyed my eagerness to learn more from her. She taught me the importance of foreplay. Every word said, noise made, touch felt, action taken, and even the current emotions we were going through could completely change the vibe during a hook up. When we were in good terms, sexual contact between us was playful and passionate. When we were just getting over a fight, sex would be rough and a little forceful.

I did notice that our Catholic schooling did fuck up the way Amy thought about sex. She believed that penetration without having admitted we loved each other might be a little sinful and slutty, but everything we were currently doing and all of her various kinks were technically okay because we weren't having real sex. I didn't really care, that fine line was blurred for me. I had no problem being into whatever Amy was into and Amy was into some really interesting things.

The stress of college applications were bothering Amy and I. We'd spend many nights together in my car or on a bed just talking about what we were going to do for the future. We were clueless at the time.

On one particular night at her place, I was lying on her bed talking about some plan on backpacking through the world if I didn't figure anything out by the time I was done with college. I was laying my hand back on the pillow when I felt something hard within the pillow. I got curious and reached into the pillow cover to find out what it was. Amy freaked out and tried grabbing the pillow back. I was able to take out this mystery object and it turned out to be a compact vibrator.

Amy started freaking out and apologizing. I told her I didn't really care. She explained that she received the vibrator as a joke gift on her birthday. She got curious and actually ended up using it. She told her ex-boyfriend about her vibrator use and the vibrator intimidated him. They ended up having a fight over it. I assured her that I really didn't give any fucks about it. I just laughed it off and joked about watching her use it.

She gave me this inquisitive look and told me that we could make this a little more interesting. She went into her closest and rummaged through one of her boxes. She turned around and in her hand was a pair of handcuffs.

There was a hero themed pep rally that happened a few weeks prior to this story. Our school gave the student government some cash to buy decorations and costumes for the event. Amy though she'd be clever and came dressed for the pep rally as a cop. She used the school's money to buy fake metal handcuffs to make her costume authentic. They looked like real cuffs, except all you had to do was press this latch on the side to loosen the cuffs instead of using a key. Technically, our Catholic just bought her a new sex toy.

I started laughing when I saw what she brought out. She wanted to play a game. The first person to get both cuffs onto the other person would win the game. The prize: they could do almost anything they wanted to loser. I was intrigued and agreed to her challenge. We went on opposite sides of her room and Amy threw the cuffs in the middle.

I ran towards the center of the room and grabbed the cuffs. Amy tackled and pinned me down to the ground, mostly because I let her. We playfully fought for control of the cuffs at first. My dick was getting hard from all the body contact and I started thrusting my hips into her. She started pushing her ass along my cock. She bent down and started licking a sweet spot on my neck. I thought the game was over. I gave her a light kiss on the lips and slowly started making out with her.

Amy snatched the cuffs out of my hand while my guard was down. She quickly latched one side of the cuffs onto my wrist. She gave out a victory cheer and quickly grabbed my other hand to attach my other wrist to the cuff. I wasn't ready to give up on this game of hers.

I immediately pushed her back onto the floor and pinned her on the ground. I removed the cuff on my wrist and tried to cuff her back. She held my arms back to stop me. This game got serious. Our wrestle for the cuffs became part sexual and part legitimately trying to gain control of the handcuffs. At some point, I took of her shirt and she took off her bra. We started taking off all of our clothes, scattering them along the floor, while rolling naked attempting to snap the handcuffs on each other.

We'd frequently stop to start making out for a moment. She would grab and jerk my dick to distract me. She'd whisper in my ear about horny she was and how badly she wanted my dick. I'd start licking her tits whenever they got in close range of my mouth. I'd grind my dick along her pussy whenever she latched her legs around me. We'd both divert our attention back to getting those cuffs on. It was wild, painful, fun, sexy, rough, and confusing all at once.

I was horny to the point where I just wanted to pin Amy down and get a taste of every inch of her body. I didn't care about the handcuffs anymore. That was my downfall. I pinned Amy back to the floor and started kissing her. I dug my hands through her hair and started reaching for her arms. I felt the cuff latch onto one wrist then she quickly moved my other arm into the empty mouth of the other side of the cuff. Amy had won the game.

She celebrated her win and told me to get on top of her bed. She removed the cuffs and then re-cuffed me so that the chain came around the openings of her headboard to limit the movement of my hand. I had lost the game, but I was excited to see what was going to happen.

Amy kissed me and then she hovered her boobs over my mouth. I desperately wanted to suck on those perfect nipples. She hovered just high enough so that my tongue wouldn’t reach. Then she lowered herself so that only the tip of my tongue could get a taste. Once she got low enough, I buried my face into those tits. She moaned for me to keeping going. I licked, kissed, and sucked as much as I could. She calmly sat straight up on her bed with this suspicious smirk on her face.

She grabbed for the vibrator that started this whole game in the first place. I began questioning her as to what exactly she intended to do with that vibrator. She just smiled and turned the vibrator on. She traced the vibrator down my chest and onto my thighs. It actually felt really good, but I started freaking on when she started moving the vibrator towards my ass.

She started to laugh when she saw me panic a bit. She was just messing with me. She moved the vibrator on my balls while she started licking the length of my cock. It sent tingles throughout my whole body. Amy then started to move the vibrator against my hard dick. At first, I didn't really feel much, but then she hit this spot right below the head of my cock. It felt fucking amazing. I started shaking and moaning. Wave after wave of pleasure started to go through my body. I wanted to grab her head and push her down on my cock, but was forced to let her continue to do whatever she wanted since my hands were still immobilized.

She turned off the vibrator and started tracing my mouth with her index and middle fingers. I opened my mouth and started sucking her fingers slowly. She took those fingers and spread her legs out in front me. She closed her eyes and started fingering herself just inches away for me. I hopelessly bucked my hips into the air and I wrapped my legs around her to bring her into me. She wouldn’t budge.

“You told me you just wanted to watch earlier,” she’d tell me with a wicked grin.

She turned the vibrator on and started rubbing the vibrator on top of her wet pussy. She slowly slipped the vibrator into herself. Back and forth. She began to whimper and moan as she fucked herself with her own vibrator. I was getting so turned on watching her. She was just inches away from me and I couldn't even touch her.

Amy turned the vibrator off and then hovered it over my lips. She told me to open my mouth and taste. I opened my mouth wide and I took the vibrator into my mouth. She moved the vibrator in and out of my mouth while my tongue frantically rolled around the vibrator to get a taste of her. She removed the vibrator from my mouth and I begged her to let me eat her out.

Amy stood above me and then she buried her pussy in my face. My tongue urgently began licking. She ordered me to go slow down and I did as she asked. She began to moan once I took my time eating her out. She reached back and started jerking my dick. I moaned into her.

She sat up on my chest and then reached for her vibrator again. She turned it back and on began fucking herself just inches away from my face. She went deeper and deeper into herself. Her breaths became faster and her moans became louder with each thrust. I remember her closing her eyes and throwing her head back as she began moaning that she was close. She began thrusting her hips as she fucked herself and then she let out one long and loud moan.

Amy collapsed on top of me and kissed me. I was frustratingly hard and horny. She slid down to my dick and started jerking me off. Just having someone finally touch my dick again felt amazing. I just wanted to cum so badly. She laid my dick across my stomach and then put the vibrator on that sweet spot on my cock again. My body began to shudder. It felt so good. She kept rubbing the vibrator against that spot on my cock. I started getting this headache from all the sensation coming from my dick. I started moaning that I'd cum soon. The headache was replaced by powerful courses of pleasure shooting through by entire body all at once. The frustration from not being able to do anything left my body and I suddenly got really tired.

Amy un-cuffed my hands and we took a shower together. We came back onto her bed and took a nap before her parents got home.

That was definitely one of the wildest moments I shared with Amy. She opened my interest into trying different kinks as I began to explore with sex over the next couple years.

This would be one of the last times Amy and I would hook up during high school. In the end, Amy brought out the three words that would kill our relationship: "I love you”. I freaked out when she said those words. I didn’t feel the same way and my first instinct was to end the relationship. I didn’t want to lie to her. She couldn’t understand what she did wrong. She said she felt used by me. It was a messy break-up. It would take months to patch things up between us.

Amy and I would eventually continue our sexual adventures throughout college. During the last few months of my senior year, my attention focused on an experience of a completely different kind.