Finally, after all my patience with this beautiful woman, I've done it with my step mom's friend, who we'll call Steph.
To start, Steph has been very flirty with me since we've met when I was 16. She always hugs me and calls me cutie, etc. It used to make me uncomfortable but eventually I realized, holy shit this woman is incredibly sexy. Steph is blonde and fairly short (5'3" give or take). She has nice C cups and a nice round ass for a white girl. She's had two kids (and she's only 27) and still looks amazing, which made her even hotter in my eyes. I've never pursued anything and always just left the flirting there, but at this point it was my graduation party, and I'll soon be moving 4 hours away. So I pursued...
During my graduation party, we were sent to the store (which happens frequently during parties, she always volunteers to make quick runs to the store for my parents and I'm asked to go along with her) and on the way I had been thinking intently and nervously about how this could be my last chance to at least pursue something with her, and I finally got to it. I figured that if anything is gonna happen, it'll happen now. So before we went into the store I asked Steph to wait to go inside cause I had to tell her something. So I told her what I was thinking.
I said something along the lines of, "I've noticed how flirty you are with me and have always wondered if you've wanted more." I sat there nervously as she smiled at me, then something finally happened...
We were in the car in a fairly empty parking lot when Steph came on top of me right after I asked the nerve-racking question about our relationship. She climbed on top of me in the passenger seat and immediately began making out with me. We kissed passionately for a while until I began moving down to her neck and began sucking on it. I was scared it would leave a hickey but at that point I didn't give a fuck. She beautiful woman was on top of me and I was gonna do whatever I could to satisfy her. My erection at this point was insane. I was so hard and my dick began throbbing and hurting from pressing on my jeans. I continued kissing her neck and her and I could hear her moans. Which made me feel amazing. I was making her moan and I just couldn't get enough. I pulled up her shirt and took of her bra and began playing with her tits while we kissed. I soon moved my way down and began sucking on her tit, which made her moan even more.
She soon took my shirt off and we continued making out. I slowly began creeping my hand down her pants and felt her pussy. It was really something special, and I don't even know why. She was incredibly wet and that made me feel so good about everything that was going on. I began to unzip her pants and eventually we took them off, leaving her in nothing but her panties. She immediately undid my belt and took off my pants and pulled down my boxers, revealing my throbbing cock, which I could tell made her excited. Keep in mind we did this all in the passenger seat of a Range Rover. She took a knee down under me (where you put ur feet in a car) while I sat and began bobbing up and down on my cock. I couldn't handle myself. I was moaning and felt like I shoot my load like a rocket into her mouth, but she stopped before I got to that point... I guess she was just getting me warmed up. Right after she asked if I had a condom, and I gave it to her. She slowly and lustfully but it on me and jumped on my dick. She began going up and down while I just sat there and she moaned softly. I was surprisingly able to control myself and didn't immediately jizz right then. I held myself for a while and figured that she would get off better if I pushed up and little bit as she pushed down, and boy was I right. Her moans got louder and more passionate and I could tell she was having a good time. Her pussy insanely wet and my dick insanely hard, we kept fucking for a solid two minutes until eventually I couldn't take it anymore, I told her softly "I'm gonna fucking cum." to which she said "do it baby" which made me feel incredible. She had just called me baby and it felt weirdly amazing. I came right after and I could believe it. It felt like ecstasy. She got off of me and knelt down and smiled at me while I was cooling down from my moment. I didn't want to disappoint her so I said "come here" and brought her up and tightly switched places with her. I began to eat her pussy, and it was surprisingly nice. I thought it was taste terribly but it didn't. I kept eating her out and hearing her moans pushed me to do it further and more passionately until I felt her leg begin to shake and she screamed out "Oh fuck!!!!" Her whole body began to shake a bit and I knew she had finished. She sat there smiling for a while.
After we were both finished we put our clothes on and went into the store. She disposed of the condom discreetly when we got back to my house. I haven't seen her since and it will likely never happen again, but it was amazing.
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