I was right at that age in my middle teens and looking for my first time with a woman. We were at the pool. My friends Bob and Mike and I were checking out the babes and talking about how we would fuck each one even though none of us had even seen a pussy or knew how to fuck a woman. Then I spied Kelly Hanson.
Kelly was a friend of my parents and I have had a crush on her since I was a k**. She was not hot per say, but something about her made me want to stick my dick in her and bust a nut so bad it made me crazy. Kelly was in her mid to late thirties, married, short tan legs. Nice c cup boobs and dirty blonde hair with pretty brown eyes. She was maybe five foot five with freckles and a thick southern accent. I am guessing she weighs around one hundred forty pounds. Again not ugly but not on everybodies fuck list.
Then it happened. As I stared at her Mike said that he heard that Kelly would let virgin guys fuck her for twenty dollars. I should have known better, but for some reason I took the BS mike was dishing out as truth. After several minutes of talking it up and the thought of busting a nut inside her, or even seeing Kelly naked was more than my brain could handle. They dared me and I took the dare. I walked over to where Kelly was laying out and pulled twenty dollars from my pocket and held it up. She looked at me and asked what was up. I told her I was a virgin and needed her to fix that for me.
Kelly's mouth dropped open and her eyes went from warm and friendly to super pissed. Kelly flew into a rage. "What the hell did you just ask me?" Kelly yelled. My friends started laughing and ran off and just as I was about to run Kelly grabbed me by the arm. "We are going to your house right now and talk to your mother!" Kelly screamed. Oh shit I was in some trouble now. Kelly grabbed her bag and lead me out of the pool. We walked down the street to her house. "I want to change out of my suit before we go talk to your mom." I sat in a chair in Kely's living room. I was scared to death plus now Kelly thought I was a creeper and now my mom will kill me. After what seemed like forever Kelly came out of her room with a robe on and sat on the couch across from me.
"I thought about things and want to talk to you before we go talk to your mother." Kelly said. "I have always liked you Greg and I think you are a real good k**." She added. So I told Kelly about the dare and everything else trying to get my ass out of trouble. So this seemed to satisfy Kelly and made her decide not to tell my mom anything.
Then Kelly said "I think I feel better about things between us Greg, now about this virgin thing? You would want me to be your first, out of all the young pretty girls at the pool and in your school you would want me to be your girl for your first time?" I thought for a minute, trying not to be shy and trying to act grown up "Well yes Kelly, I would want you to be the one." I said thinking that now I could leave and run home. "I want you to promise me that you will never tell a soul about what I am going to tell you, promise me." Kelly said. I promised her, waiting for what she had to say. Kelly got up and went to the kitchen and came back with a tall glass of wine. We sat there looking at each other as she drank the wine, me waiting to hear what she had to say. After about five minutes and the glass was now empty Kelly stood up and went to fill the glass again. She returned and stood in front of me, took another swig of wine and set the glass on the table then she looked me in the eye and opened her robe and dropped it to the floor.
Kelly was now standing in front of me completely naked. I could not believe it! I stared at her body, her tits, freckles, her wonderful bush, her legs, more of her bush. I was like a deer in the headlights, I could not move, but my dick could and it went to hard as steel in half a second. Kelly asked me to stand up, "I am not sure how to do this as I have never had a virgin before." She said. I stood and Kelly started to kiss me and rub her hands all over me pulling my shirt off then pulling my swim trunks down. My cock stood straight out with precum dripping off the tip. Kelly knelt down and took my cock in her mouth and sucked it gently.
This was like a dream for me. then Kelly laid on her back on the floor and spread her legs. Her pussy was more hairy than I thought it would be but it was wet and her lips were wide open. I moved in on top of her and she guided my cock into her. I was trying to hurry but still trying to be cool. Sliding into Kelly was the most amazing feeling ever. I pushed my cock deeper and deeper into her till I was all the way in. Kelly was breathing hard and I started to pull back and then back into her my cock was so hard it hurt and I knew I was about blow any second. "You feel so good inside me, do you like the way I feel?" Kelly Asked. I told her she felt great and that was all I could do and my cock exploded. Kelly moaned as my cum flowed into her and she wrapped her legs around mine and her arms around me holding me tight. I must have cum a gallon as cum was all over both of us.
I stayed on top of Kelly with my still hard buried deep inside her wonderful cunt. Kelly asked "How was that for your first time?" that was amazing but I not done yet." I replied and I started to fuck her some more this time lasting much longer before filling her womb with more of my cum. This time I rolled off of Kelly sat up and stared at her. She laid there with her eyes closed looking very content and happy. She opened her eyes for a second and told me she loves getting fucked. I looked at Kelly's body, her cum soaked hairy cunt. I had imagined her cunt would be shaved, and her body would be more thin with perky tits. Kind of funny how things are always different than what we imagine they would be I thought.
I became Kelly's man on the side, we would sneak around and fuck every chance we got. Kelly seemed to get off teaching me what I need to know about fucking. She wanted to hear about my dates and all the details about my fucking other girls. I would give her the details and then she would fuck me silly, she really got off on me fucking other girls. So much so Kelly wanted to smell the pussy on my fingers and cock, I was not to shower after fucking other girls. Kelly had always said she wanted to have another woman join us but that hs not happened yet. I continue fucking Kelly to this day, it has been fifteen years since this story started.
Posted by zimabean 5 months ago Views: