How I Broke My Best Friend’s Cherry

Story submitted by: Jon

I am Jonathan and I would like to share with you guys my ‘First time’. It all started when I was sixteen years old, I had a very close friend named Skylar. She may look like an average girl, small and slim, tall about 1.7m, size 24A, but she had a great complexion and looked amazing even without make up.

We were in the same class for four years and when we had reached our final year, we frequently met up to study together, although most of them ended up with us playing.

One day, when we were studying in the school library as usual, we were quite focused on our revision, with our ear pieces plugged in. Both of us did not realize that it was almost 6 pm and the school library was closing. After a while, I had decided to take a five minute break. I looked at my phone and to my shock, it was already 6.30 pm.

As we always sat in the corner seat behind the shelves of books, there was more privacy. It meant that it was hard for the librarian to spot us before locking the library doors.

I quickly shook Skylar to tell her that we were locked inside the library. At first, she seemed annoyed that I had disrupted her from her revision, but after she realized the situation we were in, she started to panic. I slowly stroked her back, trying to reassure her while frantically trying to think of an idea to get us out of here.

I checked my phone and realized my phone was about to be dead and Skylar had forgotten to bring her phone as she rushed out of her house today. I started to think our parents will definitely look for us.

I asked her, “Your parents! If they realized that you’re not home, they would definitely call the teachers, and they might find us trapped here… How are we going to explain to them?!”

She replied in an anxious yet calm tone, “It won’t work, Jon. They are overseas, my older sis is staying in a hostel, no one will know if I am home or not.”

My parents were overseas too. As we looked through our options, the choice of us spending a night was the only way.

As it was only about 7 pm, we had decided to make ourselves comfortable for the next twelve hours in the library. As the school was closed, we will not have to worry about what we did.

Sneakily, a dirty thought came to my mind as I was going to spend a night with a girl I had a crush on for a long time, why not make it memorable.

As we sat on the library’s sofa and laid back, I placed my arms around her and she naturally leaned towards my shoulder as we usually did. She was feeling tired and I was thinking about the plans I was going to do with her tonight.

As I looked through my options, there were three things I could do:

First, I could confess to her and making out would be easy if she accepted, but if she rejected me, I would have to deal with the embarrassment throughout the night, not forgetting the awkwardness.

Second, I could not do anything and just let the night pass normally, but the opportunity would never come again.

Third, I could try my best to light up the atmosphere by trying my luck to turn her on, maybe we could have sex.

As she was rather innocent and naive when it came to this (Not to mention she had not even lost her first kiss.), I had decided to take things slowly. As my arms continued to be over her, I started twirling her long hair.

She leaned nearer to my face as we continued to talk to let time pass. I asked her this question out of curiosity, Skylar, have you ever made out with a guy before?”

She instantly stopped, sat up, looked at me in the eyes with a little confusion, “Why would you ask me this question when you already know the answer? You are the only guy I have been this comfortable with.”

As I knew I had the advantage in continuing this conversation, I proceeded to set the mood right before escalating it. As I placed one arm around her waist and brought her closer to my chest, I placed another hand on her left thigh and whispered into her ears with a rough and mischievous voice, “Aren’t you curious about how it feels to make out with a guy?”

She looked at me with her cute puppy eyes and answered like an innocent little girl saying, “A… A little, I… I… I guess!?”

Staring straight into her eyes, I knew that it was time to act. I pulled her leg closer to me and pinned her down onto the sofa with my body on top her as our faces were just centimeters apart. My body was pressing against her, I could feel her boobs against my chest despite the size, not to mention her racing heart. I leaned my face over to hers and kissed her lips.

When our lips touched, it felt like magic. As she shut her eyes, enjoying the moment, I slowly pushed my tongue into her mouth as we escalated to a french kiss. Our hearts started beating faster, I felt heat rushing through my entire body. It was amazing as we continued until what we wished was an hour because of how enjoyable it was. As I stopped kissing her, she did not dare to look at me in the eyes. She was clearly embarrassed as it was clearly written all over her flushed face. She gently pushed me away and sat upright, recovering herself from the lewd position we were in.

I placed my arm around her waist and I started rubbing her thighs. I moved my body to sit closer to her as my hands gently caressed her legs, moving slowly towards her inner thighs. I lifted up her skirt as I moved my hand closer to rub her breathtakingly moist pussy. I felt like I had won a war! To touch my crush’s pussy? Isn’t that all men’s dream? It felt so good… So good, my soldier was standing upright despite touching it with only the tip of my fingers.

I did not hesitate to rub her precious jewels in reciprocating motion. I could feel her breath getting heavier as she made soft moans. Soon enough, my hand was covered with love juice. I knew she was getting really turned on by it.

I could not take it any longer. My soldier would like to be at a place I called the sanctuary. I spread her legs as I positioned my body in between them. I went on my knees and pushed up her skirt as I took off her panties. It was drenched as if it was caught in the rain. I started to unbutton her school uniform and to my surprise, she did not resist. As I took off her shirt, I stopped to admire her beautiful body that turned me on. I said in a firm yet seductive voice, Skylar, show me what is underneath that bra of yours.”

She looked as red as a tomato and said, “A-alright…” She unhooked her bra, showing what to me was a godsend. I grabbed it and threw it on the floor as I pinned her roughly on the couch, started playing with her cupcakes. As she had a petite body size, it turned me even more. I placed my finger over her small pink nipples and started rubbing it gently. *Pause* As each rub passed, it got harder and harder and her moans became louder and louder. I placed my mouth over her left nipple and started sucking it hard with random gently bites. Skylar moaned, “Ahhh… Baby please don’t ahhh… Stop.”

I went even harder as I squeezed and fondled with her breasts. I slowly lowered myself to position my face just at the entrance of her pussy. As I looked and admired her clean shaven virgin pussy, I proceeded to rub her pussy with my fingers. As I slowly inserted my left middle finger, she moaned loudly as I continued to finger her. I added my index finger and instead of going half a finger, I pushed the entire two fingers through, she screamed loudly, “Babe please, pain, very pain.” I slowly pulled out both fingers and started rubbing her clit, while inserting my fingers gently. As her breaths quickened, she started moaning crazily, “Ah… Babe don’t stop I’m cumming…”

As she had her first orgasm, her pussy was squirting for the first time, I continued to lick her pussy as I took her love juice in. I placed my finger into her mouth and told her, “Suck, taste your cum.”

I stood up and took off my clothes as my shirt was now wet with her cum and she took off my pants and underwear and my dick sprang up into attention. She gasped, looking at my dick, my dick was about six inches, longer than most Chinese guys. She looked into my eyes and said with a shaky voice, “Babe, I… I don’t that could fit into my mouth, let alone my pussy.”

The way she talked turned me on even more, I told her in a menacing voice, “Oh, don’t you worry about that fitting to your mouth and I will be rough, really really rough.”

I placed her head as I pinned it against the wall and I pushed my dick into her mouth, I started slowly, going halfway, going in and out. As soon as she was getting better at the pace, I took it to the next level, I started fucking her mouth, going in and out fully. As she gagged trying to signal for help, I didn’t care as I went all the way. I felt my dick twitched and I knew I was going to cum soon. I fastened my pace as she was struggling to breathe and I released my load in her mouth. As I saw her gulped and swallowed it, I felt so satisfied. I took my cock out of her mouth as she took a few moments to regain her conscientiousness. She stood up and gave me a kiss, pushing some cum into my mouth. She whispered into my ear, “That’s for being so rough when it’s my first time giving a blowjob, how does it taste?”

I grabbed her bare ass with my hands and replied, “Salty, but you were fantastic.” I carried her into a missionary position as I laid her on the sofa. I positioned my dick at the entrance of her love hole, she nervously said, “Jon, please be gentle, I doubt I can fit that all in.”

Although in my mind, I was secretly planning on going all out and banged her hard, I knew that the amount of pain she would go through was crazy so I decided to go slowly. I slowly inserted my dick into her going about two inches in, I saw her grabbed the sofa hard as she shut her eyes tightly. I proceeded to enter slowly till my entire shaft was in her. As I tried to go all in I felt a strong resistance, it was her hymen. I stared into her eyes and said, “Babe, your virginity is mine.”

I pushed my dick all the way and felt a sharp pain as she screamed, I had just broken her hymen. As I continued to slowly pump her, her sounds of pain slowly turned into moans of pleasure. As I felt her breathing pace fastened, she moaned, “Jon faster, I’m about to cum again.”

I grabbed her butt with my arms and carried her up, she was resting her entire weight on me while I was standing furiously pumping her. She was screaming with moans as she and I cummed together.

I placed her down on the sofa as I pulled out my dick, the mixture of cum and blood flowed out of her pussy onto the sofa. I sat on the couch as I hugged her, whispering gently into her ears, “I love you.”

She replied as she stared into my eyes, “Me too.”

We kissed as we knew something new in our lives were about to begin. We cuddled naked together under a blanket on the sofa as we slept.


Source: Jon

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