Where it happened: The Living Room
Langauge: English
Sex: Male
Rating: 5
Category: Straight
Mary and I dated in the beginning of my freshman year of high school. We had the same group of friends and she was very attractive. She was 5’9″ with long dark hair and crystal blue eyes. She had full and soft lips. She played volleyball so she was impressively fit, that and her large breasts stole the interest of a 15 year old self. The relationship didn’t last very long, but our friendship thrived even when I dated someone else.
I thought about giving my virginity to this other girl, but before i could it was revealed to me that she was a cheater. It upset me to think that I could offer that special part of myself to someone who didn’t value it. The romantic idea of a special partner for losing my virginity was destroyed for me in that moment.
By chance Mary lived across the street from me, and by the end of the year we had started walking home together, and would talk, but tension started to build in the way it so often does with teenagers. My mother worked late so I invited her inside and we kissed and started messing around. The moment it started to progress, she stopped me and said that she didn’t want to. Her main worry was that it would upset her religious parents. She was horny but I could see this tremendous conflict build inside her. I told her it was alright, that I didn’t want to pressure her, but i left her with three important ideas: 1) That I was ok with just fooling around the way we had been. 2) That what she did in her life is her decision, not her parents. and 3) That if she changed her mind, I would be honored to be a part of her life that way.
One day, after the usual trek to my house with her books in my hand, my heart racing and the pressure in my pants, we began to kiss and let our hands wander as usual. She stopped me and looked me in the eyes and asked me if I wanted to go all the way. I got so excited and must have asked her, “are you sure?” a million times. It was silly really. I put on a condom, kissed her, and asked her one last time if she had any doubts.
She laughed and said, “At this point, I’m pretty sure.”
So I entered her. All I could think was how warm she felt.
When it was over I walked her partially home and remember having that surreal feeling that I missed something. Sex was supposed to be this huge life changing moment and it wasn’t.
We spent the next few months exploring one another sexually, but I struggled with the concept romantic sex for a while worrying that I had made a mistake with her. It wasn’t until much later I realized that the act of losing your virginity is rarely special; it’s usually awkward and inexperienced. What is important the value for the person.
Mary and I are still friends today.
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