NEVERcummingback's Blog

The best sex I ever had.

The sex was with a former friend’s mom who was and still is best friends with my mom. Cindy was in her late 30’s at the time and she was also married. She has one son who I was friends with for almost six years all through high school.

By the time we graduated high school her son, Randy, had become a complete ass and thought he was better than me. He started out as a nice enough guy, but then as the years passed he became such an obnoxious ass that there were only a few people who still liked him or hung out with him by the time graduation arrived.

Randy enlisted in the Army and moved away right after graduation. Cindy’s husband is a civil engineer and travels a lot for his job as he oversees highway construction projects all over the Midwest. One day my mom told me that Cindy needed some help moving stuff around her house and with her husband and son both gone mom thought I could stop by after work and help her out.

So I stopped by after working my summer construction job the next day. I get there and I am still dirty and messy from the day of work outdoors. I told her that I was sorry I was so dirty, but I just got off work. Cindy had me help her move a dresser out of her son’s room and into the garage as she wanted to paint it.

She ended up asking me what had happened with her son and I. I told her a sanitized version of what had happened making sure not to blame her son as I didn’t want to hurt her feelings. She told me she was sorry and that Randy had some issues with drugs and … It turns out he joined the military to avoid starting his adult life on probation.

We had some pleasant conversation, but eventually I left and went home and got cleaned up. A few days later my mom told me that Cindy needed my help again. That she would like it if I would be able to stop by for a couple of hours on Saturday. It was a non work day for me so the last thing I wanted to do was house work, but she was nice enough and I had guessed that she was lonely now that it was just her in her house most days. So Saturday morning I got up, took a shower, got dressed and headed over there. She had finished painting that dresser we had moved and needed my help to move it back into the bedroom.

We made some small talk afterwards and she fixed me a drink. She sat down on the couch next to me and put her hand on leg. She started telling me about how much she missed her son and how lonely she gets with her husband not being around. As she looked into my eyes she told me she was thankful that I was willing to help her. At this point I still just thought I was there to move furniture. At 18 I was pretty naive.

When I didn’t pick up on her first overture she started more aggressively flirting with me. Rather than passively just having her hand on my leg she started squeezing my leg and slowly moved it up closer to my cock as the conversation went on. Even if mentally I didn’t get what she was doing right away my dick sure did as it quickly got completely hard. The light bulb finally came on when she put her hand on my erection and slowly licked her lips. I told her she was beautiful and that I wanted to be there for her. Then I kissed her and for some reason I was still surprised when she kissed me back.

My hands began to wonder and they soon found her D cup breasts. I groped her for a good ten minutes as we continued to kiss. Finally, I broke away from her mouth and I told her I was willing to do whatever she wanted. She shot me down telling me that we had already gone too far.

I finally found my courage as I told her I wanted more and that it was now or never. I told her that I was going to her bedroom and asked her to come with me. I didn’t really think it would work, but she said okay.

Once we got into her bedroom we started kissing and touching. I undid her jean shorts and let them drop to the floor. She pulled her t-shirt up and off and was standing there in just her bra and panties.

I undressed and soon my 7 inches of manhood was pointing straight up and eagerly anticipating what was to come. She rubbed it and said that she knew this was wrong, but that she wanted it so bad. She took her bra off and I saw her tits. I pulled her panties down and saw a neatly trimmed bush up top while the area around her pussy lips was completely shaved.

We got down on the bed and without any other foreplay I slid my dick into her. I was eager as it was my first time, but I didn’t tell her that. Obviously I didn’t last very long, but I don’t think she realized I was a virgin. I came into her pussy and it felt so good. Cum was everywhere, but she didn’t say anything.

TO BE continued....

BY NEVERcummingback