A Rock and a Hard Place

A Rock and a Hard Place

This is a true story. Character Names have been altered or changed.

My name is Drew. I’m going to share the story of how my sex life began and the romance that was never resolved. I wasn’t the best looking kid or the most popular. I just always found a way to get it done with girls. I am 6 ft. 165 pounds. I have big muscled arms and legs and a solid 4 pack. I have a thick 7 ½ inch cock and a nice ass from what I’ve been told.

My story began when I was in seventh grade. I met a beautiful half Asian half white girl named Robyn. She is 5’3 and maybe 100 lbs. She has small cherry bite tits and nice white soft skin. Her eyes are slim and cute when she smiles and she has thin but nice lips. Her long beautiful jet black hair flows down almost to her large ass. She was quirky, cute and silly so I was immediately attracted to her mind and body. We sat next to each other in multiple classes and we would always play around and flirt. One day she even let me rub her panty-covered pussy under the desk in science class. I never told her I liked her and we never got together until that summer.

We were talking a lot over the phone in the beginning of the summer and she eventually invited me over to her house to “help her with an essay”. We were both straight A students so there was no way she needed help. She had a nice two story house and we had the whole thing to ourselves. We were in the office room in her house. She was sitting in the rotating computer chair in front of me and I was standing right above and behind her. Before this, neither of us had experienced our first kiss.

I started to play wither her beautiful long hair and make small talk with her. Before I knew it, I was leaning my head down to hers and our lips had come together in a beautiful pair. I first kissed her gently. Then our lips parted and joined. After a few soft kisses, I gently stuck my tongue into her mouth and massaged hers. Our inexperience caused us to have to come up for air and we both smiled at each other. She stood up and took hold of my hand so that she could lead me into her room. I slowly reached up to her face and peeled her glasses off. I brushed the hair at her face and looked at her beautiful brown eyes uncovered for the first time.

I leaned over and kissed her passionately and with no remorse. My hands flowed through her hair, down to her back, and onto and all over her nice big ass. We made out for about 3 minutes until I decided to make a move. I took one of my hands off of her beautiful globe of ass and ran it up past her stomach to the buttons on her blouse. We spoke for the first time since we started.

“Wait. Drew I don’t think I’m ready for this” she looked at me with fear in her eyes.

“We’re not gonna do anything I just want to see what you look like ok?”

“Ok but you go first then I’ll go!”

I agreed and proceeded to take off my blue shirt and reveal my structure. She rubbed her hands up and down my abs and kissed on my chest as I pulled my basketball shorts down with my boxers. My cock sprang out and she jumped back.

“Oh my god that thing is big! I’ve only seen my big brother’s once by accident and it wasn’t even half this big” as she finished her sentence, her hand made contact with the head of my cock for the first time. She started feeling all over it and stroking it. I was in heaven, her hand felt much better than mine.

“Keep doing that oh it feels good Robyn” I moaned as her hand moved up and down my shaft. I felt like I was about to cum so I abruptly told her to stop and removed her hand. I didn’t want to put her into shock by blasting a load all over her clothes. I watched as she apprehensively unbuttoned her blouse and let it fall to the floor. She was wearing no bra so her tiny tits came into view I pinched one and gave the other a quick lick before she pushed me back and slowly lowered her skirt and peeled off her tiny cotton panties. We stood before each other completely naked.

Thankfully, I had seen a lot of porn so I knew exactly what to do. I didn’t bother trying to penetrate her with my fingers. I reached out and rubbed her outer lips and she let out a sigh. I started to look for her clit and when I found it I began my assault on her sex. After a minute of her moaning and sighing I stopped.

“Wait don’t stop Drewy that felt amazing” she pleaded, but I had other plans.

“I want to try something I saw on this video the other day” I winked at her and she told me I was disgusting. I laid her onto her queen sized bed and got on my knees in front of her. I moved my head down in between her legs and got a faint musky smell that must have been the combination of her juices and piss. Her hairs tickled my nose as I got closer to her clit. I ignored it even though it was strong and I started to gently kiss on and around her clit. She was letting out small oohs and ohs until I put my mouth over her clit and started to lap at it with my tongue.

As her moans got louder and louder I would lick her harder and harder. Eventually she stopped moaning and her legs began to tremble. Juices were filling my mouth and going onto my tongue. They were bittersweet but I enjoyed the taste and swallowed all of it. She was screaming at the top of her lungs as her first orgasm ripped over her.


When she finally came down from her orgasm and gained some control of her hips and legs I let go
of her and sat up on the bed.

“It’s my turn now Robyn make me feel good too”

She lagged her way down to the floor and started to stroke the bottom of my cock and kiss the head. I
knew she wouldn’t be able to take the whole thing inside her mouth like the pornstars do, but I didn’t’ care it felt amazing. She licked and kissed at the head for a while and then tried to take it into her mouth. Three of my inches immediately disappeared into her mouth and she started bobbing her head up and down on my cock. All the while she was stroking me with both hands so it felt like she was deep throating me. I couldn’t handle it for very long and I pulled my cock out to shoot a gigantic load all over her face and chest. She looked beautiful covered in my cum.

She got a towel and we wiped ourselves off. I asked her if she wanted to lose our virginities together and told her it would always be our little secret. After some convincing she agreed and I laid her down on to her bed once again. My semi hard cock was in my hand and I placed it at her opening. Just when I was about to thrust, fate came knocking and by fate I mean her father.

We heard the door open from downstairs and both of our hearts sank. Without making any noise, I got up and got all of my clothes on along with her. When we were both dressed she put on some perfume to hide the smell and went out to greet him. I hid behind the bed and after 5 minutes of boring small talk he went to his room and closed the door. I took this opportunity to get out of the house and catch a bus home. I would be in enough trouble with my parents I didn’t need to get my ass kicked as well.

That whole summer, me and Robyn hung out together and fucked around. Every time we were about to fuck we would be distracted or interrupted so we eventually gave up on losing it together. By the beginning of the school year we were dating, but we let school get in the way and broke up. I started to date a blonde girl named Molly. She had all of the same attributes as Robyn, but she was taller and had beautiful blue eyes.

Molly was in leadership and would always take me out of class for a quick blow or lick. She never wanted to actually have sex, but I didn’t really care because she knew how to deep throat my big cock and she was never shy about taking my load all over her face or down her throat. Naturally, Robyn began to get jealous so she told me she wanted to hang out as friends.

We were walking around her neighborhood and we wandered into an alley. Robyn forced me against a wall and shoved her tongue into my mouth, I had no objections and I returned the kiss and grabbed her giant ass for the first time since summer. We told each other how much we loved and missed each other and soon she was on her knees doing her duty as a woman. She had picked up some dick sucking talents somehow as she was able to take it all the way down her throat. Her tiny eyes and nose looked cute as she struggled to swallow my entire load that I soon shot into her throat.

I had just realized that I was cheating on Molly when I pulled my shorts back up. I guess I didn’t care very much as I stuck my hands down into Robyn’s shorts to find that she started shaving her pussy. It felt smooth as a baby’s bottom and I enjoyed it while I fingered her to an orgasm right in the alley. I’m sure some people either saw or heard, but it seemed to excite both of us.

When we were done, we made a promise to keep it a secret from our partners and act like it never happened. The rest of the year progressed normally until Robyn and I realized that we were not going to the same high school.

“Drewy you can’t not go to Granada! Everyone is going there how can you just leave me I thought we were friends!”

“We’re best friends Robyn” I explained “But my parents don’t want me to go to Granada so I just can’t. You’ll always be important to me though.”

Our graduation day was a solemn day. We did nothing but hug each other and basically said goodbye. I was in a funk for the year of 9th and 10th grade because I went to a school predominantly filled with Mexicans and they weren’t really my type. I did meet a girl named Ilse toward the end of the year and she was nice enough to give me an end of the school year blowjob in the bathroom. Besides that I just went to parties and hung out.

I started to spend a lot of time with my neighbor Javier who lived across the street. He had a girlfriend named Hazel and she wasn’t the best looking chick but she was nice and petite and had beautiful Hazel eyes. I never told anyone this, but I often jerked off to the idea of making her cheat with me and bouncing her tiny body on my hard cock and making her scream.

During the summer heading into 11th grade, Robyn and I started to hang out a lot. I switched schools to a school that was much closer to where she was, so we just happened to run into each other. She was a tennis player and I was on the basketball team. While she was at practice, I traveled to Granada for a midsummer scrimmage.

After we clobbered their team on their home floor I looked over and saw Robyn. She had gotten a little taller and gained a little weight since the last time we met and her boobs had definitely filled out nicely. Thank the heavens her giant ass was still intact. She was hot and it was clear we were still hot for each other. We hadn’t been talking much but we were still close friends and I knew it was finally my time to have her.

An hour of small talk later and we were underneath the bleachers making out and touching and grabbing each other. She was stroking on my cock and I had two fingers up her shaved twat. We were moaning into each other’s mouths and she was juicing all over my fingers. When she came on my hand she took each one of my fingers into her mouth and sucked them clean. Then she got onto her knees and deep throated me until my entire load was in her belly.

We decided to go out and everything was going good until our grades started to drop. Before I knew it, I was off the basketball team and sent right back to my old school by my father. Needless to say we broke up and even though I was depressed, our respective grades rose again. We decided to stay friends, but we got into a huge argument about not wanting to have sex and decided not to talk to each other again.

Finally I was a high school senior and at the top of the food chain. I got myself out of depression and dropped all of the weight that I gained. Javier was still with Hazel, but I didn’t really have anybody. That all changed in Spanish class one day when I met Abby.

Abby was a beautiful Mexican girl with nice b cup tits. She was about 5 foot 4 inches and she was a nice slim girl. Her ass wasn’t big, but compared to her waist it was gigantic and she had large beautiful brown eyes and flowing brown hair. I was attracted to her immediately and she was attracted to me. But deep down I knew why. She reminded me of Robyn.

Abby wasn’t a virgin which I didn’t like, but she was such a sweet girl and I liked her so much that I didn’t care. She brightened up my days and nights and she was the perfect make out buddy. She told me she didn’t want to have sex for a while, but that was all I really wanted at the time so I was going to break up with her.

The day I was going to break it off, we were in my room with no one else home. She wanted to make out but I didn’t want to. She told me she knew what I wanted and started to undress. I watched in awe as her amazing body came into view for the first time. Her tiny nipples were hard like rocks and she had a perfectly flat stomach leading down to her tiny little pussy. She wasn’t a shaver as her bush populated her mound proudly. She pulled down my basketball shorts and boxers and immediately went to work on my cock with her mouth. She wasn’t very good at blow jobs, she bit me and I didn’t cum but it was a start. I laid her down onto my bed and licked at her clit. Within minutes she was screaming and squirting juices all over my face. It was the most cum I had ever seen from a girl.

My father came home right before I could fuck her. I was so ready but at this point I felt like it was a sign that I would probably be a virgin forever. It was like god or fate was being the ultimate cock block. I snuck her out through the back door in my brother’s room and walked her home. Needless to say I didn’t break up with her.

Abby really started to grow on me and I started to feel bad about that way I talked to people. I was born with the gift of intelligence and I started to realize how much of an arrogant tool I was to my old friends including Robyn. I decided to call her up and smooth things over so I could exorcise all of my demons and move on with my life with Abby. That’s where all the trouble began.

In retrospect, meeting my ex who I had intense feelings for under the moonlight at a park probably was not the best idea for me and my new relationship. We met and started to apologize for everything. Just as I was about to leave, Robyn stopped me and let everything out.

“I love you Drewy I think about you all of the time. I just want you to be happy and I know you’ll only be happiest if you’re with me and I’ll only be happiest if I’m with you”

“I love you too Robyn, but only as a friend, our time has passed and I found someone. I’m sure you’ll find happiness somewhere you just have to look”

I lied. I felt the exact same thing but I wasn’t going to ruin what I had with Abby, or so I thought. My declaration went through one of her ears and out the other. She rushed me and kissed me. I was too weak mentally to fight back. We embraced and tongue fucked each other’s mouths until we were sore.

“I want you to take me Drewy. I was so wrong I want you to take me right here in this park”

I was going to do it. I was going to release all of my emotions into her, but fate came knocking once again as my brother James called to tell me that he was picking me up in a couple of minutes.

I told her that I couldn’t do this and this was the last time we would see each other. She didn’t believe me and said I would fuck her and be her first, but she wasn’t going to sabotage my relationship, we decided to just be close friends.

Later that day, I tried to explain to Abby that my best friend was a girl and she didn’t seem to like it.

“As long as you guys don’t have any history of being together I guess its ok” she said

“No not really we’re just really good friends and we talk about life and everything”

To Be continued…

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