I’ve written already about my actual first time but I’d like to tell a little about the one who really left that lasting impression on me.
I had a fiance and had been with her for quite awhile. We had our own apartment in a shitty building. I met Jessica through a few female friends. Jessica was younger than me but was extremely beautiful and looked older. Of course I was far from a virgin and she knew that I had sex with one of her friends. I started out driving her home. I was the cool older guy with the nice car I guess. After knowning Jessica for a few weeks I started flirting with her and to my suprise she would flirt back.
Jessica knew about my fiance. She was in fact friends with my fiances younger sister. One night while parked in her driveway after driving her home, I decided to let her know how I was feeling about her. She kind of smiled at me. I leaned over and tried to kiss her but she refused. So I grabbed one of her breasts and started rubbing her nipples through her shirt. After a few minutes of this I pulled up her shirt and exposed those beautiful tits. Her nipples were tiny. I started licking her nipples and then sucking lightly on them. Her mom came to the door and we stopped everything and she got out of the car.
A few weeks later we were at my place, I had a friend over and he was sleeping on the floor. Jessica was on the bed with me, my fiance had left for work. I started out putting my hand under her shirt and playing with her tits. I knew that she had only had sex once before so I was hesitant to go too fast with her. I put my hands down her pants. She had minimal hair down there, she shaved. Her pussy was so warm and wet as I inserted my finger. This went on for a few minutes before I took her pants and panties down to get better access.
With my buddy still sleeping I asked Jessica if we could have sex. She gave an approving nod and I climbed on. I dont believe I used a condom. I put the tip of my dick into her and slowly pushed in. I’m not the most well hung but I’m not lacking in that department either. Inch by inch I kept going farther and farther into her wonderful pussy. I moved in and out but with only about 1/3 of my cock in her. She loved it but as I put more and more in I could tell from the look on her face that it was hurting so I pulled out. I tried to kiss her but she once again moved away and said “kissing is too personal”.
We decided that day that we would fuck all we wanted but we wouldnt kiss. Kissing was just too personal and it would lead to other things, things like feelings.
A few days later Jessica came over again. We were alone and this time I wanted to go down on her. I pulled off her shirt and started playing with her tits. I started licking them and then slowly went down to her navel. I undid her jeans and pulled them and her panties off. It was the first real look of her pussy that I had. It was beautiful. I was immediatly bent down and started kissing all around the outside of it. Then I lightly touched her clit with my tongue. She inhaled sharply and I could tell she liked it. I ran my tongue down the length of her slit and inserted the tip of my tongue into her hole. She loved it. I got up and stuck my dick into her pussy and this time went all the way in. I started thrusting in and out. She wrapped her arms around me and held me close as we fucked. I asked her to bend over the couch which she did with out hesitation. I got behind her and inserted the tip of my dick into her from behind and slowly inserted it all the way. We went at it for a little while until I finaly pulled out not wanting to cum inside of her.
Jessica and I continued to have sex over the next months. Sometimes it was once a week and sometimes it was daily or several times a day. I remember her trying to give me her first ever blow job. I was parked under a street light in a housing community at 2am in the morning. It was to this day one of the best blow jobs I have ever had. We used to have sex in the car, my apartment, my mothers house and just about everywhere else. We were always together. She moved in with me and my fiance after awhile. I remember once I got them both to agree to giving me a full body massage with me naked and both of them topless and in thongs. Even after all of this my fiance hardly suspected a thing.
One day in the passion of the moment Jessica and I kissed. Things were diffrent from that point on. We had always stayed away from kissing because it caused feelings. While I may have had some feelings for Jessica before this they intensified by 1000X after that one kiss. It was one of the most beautiful and yet sexy kisses that I have ever had.
I remember one time cumming in Jessica without a condom. It was one of the last times we had sex. We were fucking on the floor near the bathroom in my tiny apartment, her legs were over her head and she was moaning. I said hell with it and told her I was cumming inside of her for once. We came together, kissed and held each other.
Shorly after this I was evicted from my apartment and had to move far away. I wanted Jessica to come with me and my fiance but she couldnt. Days after I moved I had decided I was leaving my fiance to be with Jessica. That night my fiance told me she was pregnant.
I have now been married for several years and have two beautiful children. I have seen Jessica several times over the years, she has even come to stay with my wife and I. Every time I see her I get fucked up in the head again. After all these years Im still in love with Jessica. She is the one girl I will never get over. I will always ask “what if”.
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