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Now to set the stage my friends mom is a fitness nut. 5’6 early 40’s fit with big fake tits and a bubble butt to match. We all have given him shit since I can remember about how she’s a MILF and would get excited when she would hug us or when she would walk around the house in her sports bra and yoga pants after she worked out because god damn she was hott. Real laid back loved hearing about us dating and drama. Anyway I’m in the basement and hear someone on the stairs thinking it’s my buddy and when I look up it’s his mom. Completely fucking naked looking at her phone and my jaw hit the ground. She must of been going to get clothes out of the laundry room that’s down stairs. Anyway she looks up and sees me, our eyes meet and she tried to cover her tits. She’s got a completely shaven pussy by the way. She turns and runs up the stairs so o get a perfect view of her ass. Literally the thing everyone has wanted to see for years and I get to see thing milf naked. She comes down dressed. English. I had to take a massive piss, so I was a second late to class. I walked in as the class bell rang… there was 1 empty desk… and guess who would end up sitting next to me… Katie. All I said to myself… “there’s a theme here Steve… you’ve got this.” Katie looks at me and smiled, I return the favor with an equally genuine smile. I said nothing to Katie. The fear was real and I felt the reality of never overcoming my fear of rejection was going to be the theme of my life. Katie ended up being in 4 out of my 6 classes that year… so I knew I had time, or so I thought.I didn’t see much of Jen during the school days… we always ran into each other in the gym after school. With my growth spurt and added weight, I became a bit of a workout fiend, a gym rat of sorts. I didn’t have a 6 pack stomach, but my overall strength grew so much I felt like fucking superman. I was prepping for the baseball season in the spring… I was going to crush it. I was going to get drafted by a.
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