The summer after my senior year of high school saw my best friend Tim move to a different state. He lived right next door and we had grown up together. I was devastated to be losing my best friend. We hung out as much as possible before him and his family were all packed up. We were in his nearly empty room the morning of the move reminiscing about good times.
"I'm really going to miss you man, this place won't be the same without you," I told him.
"Robby you'll be fine bro, we are both going to leave for college anyway," Tim said.
"Yeah I guess you're right," I responded. "Hey you guys met the family who bought your house right? Did they seem cool?"
"Dude I forgot to tell you. The mom is a total MILF. If there's anything good about this for you, it's that," Tim told me.
"I don't know man, I think I'd rather have you here for the summer," I said.
"Thanks man, but I'm telling you she's one hell of a smoke show," Tim assured me. We talked a little longer before his parents told him it was time to leave. We said our goodbyes and I was left feeling somewhat alone for the rest of the summer.
The very next day, the new family moved in and I got a glimpse of the new MILF next door. Even from a distance she was everything Tim made her out to be. She had this dark brown, almost black hair. She was maybe 5' 5" and fit. She was younger than I expected. I would learn she is only 28 years old, despite having two kids aged five and seven. Her name was Tessa.
Tessa and her husband married and had kids young. They moved to the area so their kids could be in better schools when they were both elementary age. Being an 18 year old boy, it was a nice consolation prize to at least have Tessa to look at in place of my best friend.
The night they moved in, I was feeling sad about Tim leaving. When we were growing up, we would stay up late and look at each other from our bedroom windows showing off toys and doing anything not to go to sleep. That night I looked toward his room but saw nothing as he was of course gone. When I turned my gaze to the master bathroom window of the house, I was in for a shock. There was Tessa, completely naked looking at herself in the mirror. They must not have bought blinds for the windows yet. She was absolutely stunning. Her shapely ass was facing me, and I could see her big beautiful breasts through the mirror's reflection. She had very tiny areolas and nipples. From the way they swayed I could tell they were natural.
I felt myself instantly grow hard. Without thinking, in an almost mesmerized way, I pulled my pants down and began stroking my cock. I have a good sized cock at around 8" when hard. I didn't think it was possible, but I got even harder when Tessa began touching herself. She reached down and started rubbing her clit. She steadied herself with her other hand on the bathroom counter. I was pumping my dick hard and fast at the sight of this unbelievable MILF.
She took her hand off her clit and moved both to her luscious breasts. She massaged them and pinched at her little nipples. It was hard to tell, but they looked like they were now hard from her arousal. The sight was too much for me and I was on the verge of cumming.
Suddenly she seemed to notice her lack of blinds on her window. She turned to look out and for an instant I saw her face look in my direction. It was at this moment I exploded and the first shot of my load landed on the window in front of me. For this reason it took me a little longer than I wanted to before I ducked down, laying flat on the floor hoping she didn't see me. I was feeling amazing from the great jerk off session I just had, but was also terrified I may have gotten caught watching Tessa.
I didn't dare look back out the window for a while. It must have been around 5 minutes before I worked up the courage to take a look. She was gone. I was relieved to not see her, but I knew that didn't mean she didn't see me. Hell, she might not have just seen me, but seen me with my hand around my cock busting a load on the window!
Every now and again I would look toward her bathroom window, hoping to see another show. However, a few days later they bought blinds and I could never really see into their bathroom again. That didn't stop me from picturing her and masturbating to mental images of what I saw.
My summer went on without much interaction between her and I. My mom and her actually became good friends, but in truth I wasn't around much. It was my last summer before I went off to college and I had a lot going on. Before long, it was time to leave. I left for my first year and hardly ever came back except for the usual break times. The school year passed and it was finally time for me to come home for summer break.
..........
When I returned from college I spent a couple weeks just relaxing at home before my summer job began. My mom told me that Tessa and her husband divorced. She still lived in the house and the kids were with her when they weren't at their dad's. My mom and her became very close as my mom sometimes baby-sat her kids when Tessa was in a bind.
During the time before my summer job started I was being a classic, lazy college kid. I slept in until the late morning and usually started my day by going to the gym. Both my parents worked so I had the house to myself. When I returned from the gym I went to take a shower. Unbeknownst to me, Tessa came to the house to talk to my mom. She knocked on the door, but I didn't hear it because of the sound of the shower. Tessa let herself in because of how comfortable she had become with my mom.
