Disclaimer: This story is purely fantasy and all parties are over the age of 18 when the sexual fun begins. And special thanks to Sexystarlet99 for helping with editing!
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I met my best friend, Dana in my junior year in high school. She was a year younger then me and happened to be in my Math class. She sat behind me and I definitely noticed her, as she was extremely attractive but a bit shy. I was also shy so I didn't really talk to anybody I didn't know. We actually didn't talk until two months into class when she randomly asked, "If you don't have a date for your prom, I will go with you." I agreed of course and we immediately became close. We did not go a day without talking to each other whether in person or on the phone (yes this was a time when people actually talked to each other on the phone.)
A few months later our friendship grew into something more. We slowly began to date and eventually became boyfriend and girlfriend. Though we experienced many firsts together, we never advanced past kissing and some above the waist touching.
One particular passionate make out session always makes me smile. We were downstairs playing a game of pool while her parents and other family members were upstairs. I happened to sit down on a stool and she came by and gave me a quick soft kiss. She then came close and we slowly began to kiss. Our tongues slowly began to touch (this was our first French kiss). We started off very slow and hesitant, but quickly got into it. Our tongues began to explore each other. With each kiss getting deeper and more passionate, she slowly sat into my lap. As she pulled closer to me, I felt her breasts press against me. Our kissing lasted about 15 minutes. But this still stands as the sexiest and most intense make out session I ever had.
There was nothing we didn't talk to each other about. We knew everything there was to know about each other. I knew exactly what she was thinking before she told me. I also told her things I have never told anybody....some things I have never said out loud again. There was just an incredible amount of trust and support that we got from each other.
After dating for about a year, things began to slow down between Dana and me. She was caught up in school work and other activities. I was becoming jealous of her lack of time for us. The previous few time we got to spend time together I would do stupid things, just to bring more attention to myself. Eventually she grew tired of my shit and broke up with me. It wasn't an easy breakup and I made her life difficult, mostly because she broke up with me a month before my senior prom. We were unable to remain friends for a few months, but as time went by the wounds healed and we became close again.
By this time I was 19 years old and in college. While in college I did meet a few girls but most didn't go past a few dates. However, I did meet one girl who was a year younger than me. She was a thicker woman named Jenna who was a bit crazy and adventurous. I met her on the internet and when we first met each other in person, the sparks were immediately flying.
We went on a date to the movies and when I took her home, we began to kiss. This kiss immediately became intense and we both agreed we wanted to do more. We then found a quiet place and parked the car. We began to kiss again and I felt her hands slide down my chest. I felt her hand on my bulge as she began to explore my body. She began to rub my hard cock through my jeans, as our tongues wrestled with each other.
My hands found her breasts and her breathing got heavy as I slid my hand over her left breast. I began to massage her breast over her shirt. Her rubbing on my crotch began to match my slow methodical massage of her breasts. Her breasts was supple and firm and I needed to feel the bare skin in my hands. I slid my hand underneath her shirt and pushed her bra above her breasts. As my hand touched her bare breast, she let a small gasp and showed her approval by kissing me more intensely.