I grew up in the suburbs in Canada and like every male at one point in his life, I was obsessed (still am) with hot mom's. Whether that be MILF porn or the neighbour mom's, every time I could I would try and jerk off to a MILF. Something about it was just so hot and it probably didn't hurt that the neighbour was a hot mom either.My family had been living in this house for a few years before one summer this single mom and her two kids moved in next door. I was about 23 when they first moved in and was immediately infatuated with this mom. She was recently divorced with two kids and had a banging body and looked like she had been pulled right out from one of my hottest fantasies. It felt like I was in a dream.
So for the next two years our families began to grow closer as my mom was also a single mom at the time with two kids. Her kids (much younger than I) also began to look at me like a sibling and it was a nice way to get to spend more time with their mom, but, they or she didn't have to know that!When we spent days at the community pool or water park I always found myself having to go home and jerk off to her after spending the past however many hours just a matter of feet away from her in a bikini. This was especially important on the days when we would exchange a little bit of flirting but nothing excessive. Just comments about how she looked in the bikini and how there was no way in hell that body has two kids. She was without a doubt my number one fantasy even though but I could never tell her... or so I thought.
The summer I turned 25, I found myself spending more and more time with her and her family (we'll call her Sarah for privacy reasons). That summer for whatever reason I was big on binging the show "The OC" and Sarah had watched a couple episodes with me. She tole me she liked it and would like to watch the whole series with me if I was interested. Of course I was interested and that decision was made even easier when I realized it was just going to be her and I. My brother and mom weren't interested and Sarah decided her two kids were too young to watch it and needed to go to bed anyways. So, "The OC" marathon nights were happening at least once if not twice a week and usually on weekends as well, it started just a couple weeks after Sarah asked me to watch it with her.
So to make a long story short -- it was one night in July and we had been in their backyard for a BBQ and visit. The night was winding down and after a few rounds of cards, my mom and brother decided that it was time to go home. Sarah wasn't overly tired and asked me if I wanted to stay and watch the OC with her, I accepted and we all helped her clean up the table and kitchen in the meantime.
After the quick cleanup, Sarah's kids went off to bed, my mom and brother went home and we were off to the basement to begin our binge. Up until this point, we had watched the OC together for like 8 or 9 nights and there had been literally zero indication that anything crazy or wild was ever going to happen. To give you an idea of what the room looked like, there were two couches in an 'L' shape with a table at the bottom of the 'L' connecting the two couches. And a TV in the corner of the room. Usually Sarah and I will lay out on a couch each but this night she told me she was a little cold and asked if we could share a blanket on one couch. I think to cover up her reasoning, she mentioned that we could share a bowl of popcorn. So she sat beside me on the couch with the popcorn, blanket over our lower halves and away we went.
Throughout our previous times watching the show, I had commented on how she looked a bit like Kelly Rowan (who played Kirsten Cohen one of the lead characters). If any of you have watched the show, I think for some Kelly or "Kirsten" on the show was a MILF she was for me anyways. These comments over time may have been the first thing to get Sarah's wheels turning or give her the idea that I thought she was smoking hot.And in this episode, it just so happens that one of the younger characters is beginning a relationship with an older mom. As the sex scene begins between the two of them, Sarah paused the show! She then looked at me and asked if I was ever interested in an older woman and what exactly did young men see in them? I explained what I thought was hot about a mom or older woman (experience, sexy bodies, mature, great breasts, just to name a few reasons ;)).
She put the popcorn bowl on the table and pressed play to continue the show. As the show continued, Sarah began to put her hand on my leg. Now, I mentioned that we never used to share a couch so this was all new territory for me and it showed. I immediately began to grow in my pants and started to panic as I didn't want Sarah to see how aroused I was so quickly. I didn't know if she would get scared off by that or what.
She just left her hand there for the next what felt like 5 hours but was probably only about 20-25 minutes as the episode ended. I was trying so hard to make sure my erection wouldn't pop out of my pants that I didn't notice her hand slowly moving up towards my groin during those 25 minutes because as soon as the credits on the episode began to play, she grabbed my cock with her hand. I gasped loudly and naturally slid over away from her on the couch. She asked me what's wrong and apologized if she crossed a line. I replied that it was okay and that I was sorry I reacted that way I just didn't expect it in a million years and didn't know if she meant to grab me like that.
She didn't say anything but scooted back over towards me so that our hips were touching again and put her hand right back on me. This time it wasn't on my cock but it was much higher on my leg than her initial grab just like 30 minutes before that. She then whispered that she was sorry she didn't ask first and then proceeded to ask me if it was okay that she played with me for a little bit. I was in shock but eagerly said that it was okay. So there we were in Sarah's basement... I felt like I was in a dream. I had her hand on my leg and she was asking to play with my cock.
After that small talk, Sarah asked me to stand and so I stood up and turned to my left to sort of face her. She grabbed the waistband of my shorts and pulled them down a bit before placing a few soft kisses just below my belly button and around my waist. As she continued to pull my shorts down, my hard cock was just waiting to pop out and it eventually did. My shorts were now around my legs just below my knees and my cock was pointing straight out at attention towards Sarah. I can picture this perfectly just like it was yesterday -- she looked up at me with those pretty green eyes -- and said "you have a great cock" while she wrapped her fingers around the shaft and then looked down at my cock before putting it in her mouth.
You know, the amount of times I had jerked off to this exact thing in two years prior to this night it was amazing I didn't explode in her mouth right then and there. I was thrilled in fact. She continued to blow me as I reached down and went under her shirt and bra to get a handful of those beautiful breasts for the first time. It was heaven. Not long after that, she took my cock out of her mouth, stood up and pushed me back down onto the couch. I took my shirt off and pushed my shorts down to my ankles as I watched Sarah undress. First she took her top off and then her shorts off, and all of a sudden she was standing in front of me in her bra and panties for the first time. I had seen her in a bikini many times before that but there's just something that much more intimate when it's her underwear. It was turning me on like crazy.
She asked me to stroke my cock as I watched her undress and first it was her bra. She unclipped it and let it fall to the ground as it felt like maybe my jaw had followed it to the ground. Her tits were incredible. Still very perky and her nipples were about a quarter sized and were about an inch long as it finally clicked for me that she was just as turned on as I was in this moment. She took off her thong as well and then put her left knee on the couch beside me before following with her right knee. We began to make out and she asked me if I wanted to fuck her. I couldn't say yes any faster than I did and it wasn't long before she was guiding my cock into her throbbing wet pussy.
She took my cock, put it towards her entrance and slowly slid down my rock hard cock. As soon as those ass cheeks reached my balls she began to grind my cock and rock those hips back and forth. She threw her head back and moaned loudly as I stuck my face right between her tits and started to play with them. We fucked in this position for a little while before I bent her over and fucked her from behind before ultimately cumming inside of her.
We fucked twice on the couch twice that night and I will say it's still some of the best sex I've ever had. We've talked about it a few times since but never again engaged in anything sexual. I think it had been a while for her and I was probably more obvious than I thought in sneaking looks at her and being flirty. I would love to do it again someday with her, I haven't seen her in a while but I bet she's just as hot now as she was then.