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Introduction:

A legendary life begins ....
THE FIRST TIME

Being born and raised in south Florida never seemed to have any disadvantages, until at the age of 13 when I went to live with my mother who just moved to Galax,VA. My parents divorced and my brother Paul and I lived with my dad while my sister Lee and baby brother Travis lived with my mother. This was ok with me because I never liked how my mother treated me and Paul and I were very close with my dad. During the summer my mother talked my dad into letting us visit with her in Virginia, which ended up us staying there for two years.

When people learned I was from Miami they seem to avoid me like the plague. Like I was some big city gangster out to steal their horses or whatever country folk held dear. It was hard to make friends as an outcast and somewhat shy young man so naturally I ended up with the other outcasts. In this town that meant Mexicans. At school I met my new best friend Angel, A slightly overweight but very nice half Mexican half American kid just a year older than me. He seemed cool to me and we would hang out almost every day and every weekend.

Our friendship got to the point where I would sleep over at his house every weekend so I could hang out with angel and his two gorgeous sisters. I had never had sex, or anything close to it for that matter but I had been interested in it for years (Since I first found my father’s porn movie stashed under the TV). The two sisters were a year apart in age but looked like they could be twins. The older one was slightly shorter but that was the only blatant difference. They both shared the dark hazel eyes, long black hair and light brown complexion.

I don’t know if Angel ever knew I liked them, or was there to see them as much as him, but the four of us would be together every weekend just the same. Although I sent so much time around them I could not bring myself to ask one of them out or maybe kiss one even though I had ample opportunity during those long nights. I would spend hours dreaming of how it would feel to kiss one of them, touch them or maybe even more.

Just when I started to think it would never happen for me a new girl came into the picture. Lisa was a three years older than me and happened to be Angel’s cousin who lived on the other side of town. Lisa had a reputation around town for being frisky. Rumor has it she was dating a high school kid who was on the football team and would seek out at night to meet him. When Angel introduced me to her I felt like she look right threw me. She was shorter than the twins and much thicker. Her large breasts were barely held in by the tight green shirt she was wearing.

I later found out that she would be staying the weekend at Angel’s house and I knew I couldn’t miss that for the world. I arrive just after school and was ready for anything. Like most stereotypical kid evenings we tried to find stupid things to do to pass the time. Angel, the twins, Lisa, I and a few other friends were hanging out in the twin’s room and decided to play truth or dare. The game quickly went from innocent to who likes/will kiss who. I shortly realized the other guys there had eyes for the twins and who was I to compete with older dudes. Everybody seemed to be too scared to try anything with Lisa.
My turn shortly came and I said truth, because God only knows what dare was going to bring. Angel asked me “Billy, If you could bang anyone in this room who would it be?”. Terrified to answer your sisters, I blurted out “Lisa”. The room got quiet after a few gasps and even Lisa seemed a little taken back by my statement. I could feel my face turning red and couldn’t wait for the next persons turn. Finally as if my prayers were answered it was someone else’s turn.

My salvation was short lived, because when it was Lisa’s turn she said “Dare”. Angel quickly said “I dare you to kiss Billy.” Without hesitation she got up from the bed, came to the other side of the room and pressed her lips against mine. Before I knew what was happening I was making out with one of the hottest women I had ever seen and everyone was cheering on. She had her eyes closed as she caressed my tongue with hers. After what seemed like a sweet eternity, she pulled away and just stared into my eyes.
After that my mind could no longer handle the rest of the people or the game, so I walked out and went to Angel’s room on the other side of the hall. I sat upon the bed and tried to let sink in what just occurred. My mind could not rationalize the feelings I was having and I felt like I was going to pass out. Just then, in the darkness of the room I noticed the door slowly open. All of a sudden the beautiful head of the nearly grown woman I had just kissed peaked into the room. “Mind if I come in?” Lisa said. “Come in” I replied while my mind was screaming and my heart was racing. She sat down beside me, looked me in the eyes and said “do you want me?” “Of course” I barely mumbled. “Why do you want me?” she asked. It took me a second to understand why that would be a question. I finally worked up enough courage to answer “You are the most beautiful woman I have ever seen, who wouldn’t?”
With tears forming in her eyes, Lisa then explained to me that her boyfriend had just broken up with her and told her she was ugly. Before the tears could fall I hugged her close and said that he must have been blind and dumb. She laughed as she pulled back and then started into my eyes. After that began the longest make out session in the history of the world, or at least I thought it was at the time, and for that moment in time she was mine. She asked me if I wanted to make love to her, I told her I hadn’t before. She smiled and then slowly made me an expert (or so I thought).

She lay down and placed my hands on her stomach and slowly helped me take her shirt off over her head. With no bra to hold them back, her very large breasts fell out of her shirt and into direct view. With only the moonlight to see by my hands and mouth did most of the work. The warmth of her skin mixed with the feelings inside me was enough to make me wonder if I was dreaming. Once I started to feel a little bolder, I slowly removed her skin tight jeans and threw them onto the floor. The taste of her sweetness I had never experienced before but it was almost intoxicating. I felt drunk with passion while I attended to her needs. After a while she grabbed my head and pulled me on top of her. There was no mention of a condom, which was good because we didn’t have any, and I positioned myself at her entrance. With my heart pounding like a freight train, not to mention sweating like a sauna, I entered a woman for the first time.

We had sex for what ended up being 40 minutes, but it seemed to go by in an instance. After we finished, she kissed me on the cheek and snuck back out of the room. I awoke the next morning and tried to remember if I was dreaming or I had just made love to a woman. I came downstairs to find everyone was gone except Angel. He said, “Sounds like you had fun last night bro!”I smiled and went to the fridge for some breakfast. Not another word was said that day, or ever again about Lisa and myself.

After that I would see Lisa around and she would smile at me and pass by. Strangely enough I never felt the urge to do it with her again, and I couldn’t even explain to you why. After that she got a new man and a few months later we moved to another county and I never saw her again. Years and years have passed and many more and probably better experiences have happened but you never will forget your first time.

If you like this one, I have more true stories from my love life I will post, the ones after this are a bit more.....fun!
17 comments

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