Showing Me The Ropes

True story about me losing my virginity about two years ago. I was s*******n and still a virgin and felt like I was behind the curve. Looking back I was trying too hard. But I really wanted to have sex with a girl and felt like the whole school was making fun of me. My older sister seemed some what sympathetic to my position but offered very little help. I even offered her money to just let me stick it in her but she turned me down. She would always tell me "it will happen not to worry." She was getting plenty of sex.

One day the two of us were out to doing some fund raising for the school band, selling this stuff. This house down the street from ours where this really crabby guy lived, I mean this guy was a major asshole, we knocked on the door and this woman answers, I have seen her only one time before. Older full figured lady with large tits and no bra. Dirty blonde hair. She seemed about three sheets to wind. I can't help but stare at her tits as my sister does her sales pitch. The woman flirts her ass off but I am not paying too much attention. We leave and my sister says to me "Wow now there is some low hanging fruit, you should go hit that and get out of your funk." "What are you talking about?" I reply. "You should go fuck that lady, get it out of your system and then you do not have worry about being a virgin anymore." Sister said. "But she is old, like mom." I said. My sister just laughed.

I thought about what she said and the old woman. And then decided sister was right so I went back over to the woman's house. She answered the door and I told her I had more stuff to show her and she invited me in. Lucky the asshole was not home. I did not even show her anything, I just started flirting and she flirted back. Next thing I know we are making out and my hand is down her shirt playing with those sweet tits. Within minutes we were both naked on the couch, her puffy pussy right there in front of me and my hard cock dying to get inside it. But I froze, I did not know what to do. I looked down at her hairy pussy and just stared. "Well what are you waiting for?" the woman quizzed. I looked at her and then back at her pussy. I never thought this would be like this. "Oh I know, just place your tongue right here on this button and lick, my hands will be on your head and I will guide you and when my hands push harder on your head you lick harder on my clit, make me cum and you get a prize." She said. I did as instructed and within a minute or two the woman was cumming real big. She pulled my face in her creamy pussy and then pulled me up to her face and kissed me as she guided my cock into her cunt. I thrust forward into her, Wow! I was now balls deep in pussy!. "Fuck me!" She moaned. I started thrusting into her picking up speed as I went. She was pulling on my butt cheeks trying to pull me deeper into her. Those tits flopping about. Her legs were wrapped around mine and I came, my cum flowed deep into her womb.

I sat there looking at her, my cock going limp inside her gooey cunt. "Well, what do you think?" she asked me. "Did I meet your expectations?" she asked. "I liked it, how did you know it was my first time?" I said. "I can tell. I am glad you liked it and I hope you want more from me, I want to have more sex with you." She said. I thought to myself why not. She let me know when her husband was going to be gone and I would show up. We would fuck and fuck. She taught me alot, she seemed to like teaching me about sex. I loved draining my balls deep in her pussy. I also liked her sucking my cock and swallowing my load. My sister figured out I was fucking that woman. "Every man needs a woman to show him the ropes." She told me.