This story happened in late june, in the early 2000s. I was just out of the 10th grade and it was summer vacation, I was 16 years old at the time. Just like a lot of my fellow schoolmates, I couldn't get laid or have a girlfriend. It was by biggest dream to have sex with someone, even if it had to be the ugliest, nastiest and fattest girl of all. I watched a lot of porn: big tits, lesbian, anal, hardcore, etc. However, there was one type of porn I was liking more and more: Milf (Mother I'd Love to Fuck). It wasn't the fact that these women had kids or whatever (since most of those in videos were only women aged around 30-45), but I just started liking older women. I started to lose interest really quickly in girls my age. I knew all I could do is fantasize, because no woman would be stupid enough to have sex with an underage guy - at least not the ones I was looking at. Milf eventually became the only porn I would look at, losing all interest whatsoever for girls under 30. It even got to the point where certain milfs looked to young and wouldn't even get me a boner.
Some Wednesday, around late june 2000-2001. I was home alone, given the fact that my two parents worked and my sister was either working or hanging out with friends. My sister was gone for a couple of days to Montreal, to see a few shows and meet with some friends/cousins to have a good time. My mom had just called me (it was about noon) and told me that she wouldn't come back home after work, that my dad would pick her up and that they would go to some romantic dinner and come home around 11 PM. So, happy at the thought of being alone for the rest of the day, I started cooking myself some lunch and played a couple of video games. As I was cooking lunch, I always looked out the window and looked at people passing by, just to make time go by faster. Where I live, there's always people coming and going, because I live in a townhouse. Townhouses have parking lots like everywhere else (instead of having private parking lots), and they were allotted to their owners. Of course, there were always visitors, so a couple of extra parking spaces were left to visitors. The one right beside my parent's car was a visitor space, so there were always different people parked there. So, I was cooking lunch and looking out the window, as I see a woman leave a house from the other side of the block, with her 3 kids, 2 boys and 1 girl. She was alone, and she looked a bit tired. She was probably visiting her parents with her 3 kids. I immediately noticed how hot she was. She was probably around 35, maybe a bit older, pretty chubby but not fat, nice tits, professional look, long black hair and a very sexy body overall. I wanted to fuck the shit out of her - I think I got an almost instant boner right there. So I just looked at her, helpless to do anything (I wouldn't even try my chances with a 30-something mother). She was helping her kids get inside the car, which seemed like quite a task. So, I just tried to forget it and go eat my lunch in front of the TV. I ate, which took me about 10 minutes, and then I went back upstairs to wash the dishes. I looked out the window, and who do I see still getting ready to leave? Yes.
She was having some sort of problem, I wasn't sure what it was. I tell myself to keep it cool. I went outside and that's when I met Michelle.
"Hey. Do you need any help?"
"Actually, I do. My little boy's getting really sick, can I use your phone?"
It turned her little 6-year-old boy was pretty sick, and when he was sick and had the symptoms of his disease, she has this number to call and an ambulance would come pick him up. I was already making plans in my head, because to be honest I couldn't control myself. All I thought about was fucking this woman. She looked 20 times hotter up close and personal, she was really nice and warm, she had a very good personnality and seemed like a good person overall.
"So when do you think the ambulance is gonna come?", I asked.
"They can take up to 20 minutes sometimes. They know this particular case with my son and it takes a considerable amount of time before he gets really sick. He just has to lay down on a couch or something"
So, the 3 kids were in the living room: one of them was lying on the couch silently, while the 8-year-old girl was just taking care of the other 6-year-old boy, which was seemingly the sick boy's twin. I offered Michelle something to drink, and she straight up told me she needed alcohol because she had a long day. I gave her a beer, but after 1 she said "I shouldn't drink, you know because I have to drive the kids home after'. So we just chatted for a good 15 minutes. I learned that Michelle was a 36-year-old single mother who's ex-husband divorced her and moved out west, and how hectic her lifestyle was because she had 3 kids and a pretty big job. We were borderline flirting, but I didn't even think it would become what it became. So, after 15 minutes, ambulance comes, and the ambulance guy said 'Hi Michelle, doing well today?', which meant he actually knew her, and this whole little boy getting sick situation was nothing new. They brought him, and just as the ambulance was about to leave, the officer said 'do you want me to bring your two other kids to the hospital? I think they're used to it now'. Right at that moment, I swear I could see myself ejaculating all over this 36 year old hottie. I didn't care how unrealistic or cheesy it was, but I knew something was going to happen if she said yes.
"Umm, sure. I really need some time off. When do you want me to pick them up? At 5PM sharp? Ok."
They left, and I was left alone, in my house, with a hot as hell 36 year old that I wanted to fuck, who was also a tiny bit tipsy. She started talking to me as if I was one her girlfriends, immediately.
"I don't know what I should do this afternoon...there's already the fact that I have to date this asshole tonight"
This was the first time she used any vulgar word since the beginning of our conversation.
"So, you're seing someone?", I replied, disappointed, but still hopeful.
"Yeah, well it's complicated. Now between you and me, I've been trying to have sex since my husband left me 2 years ago. But all those losers I date are looking for some sort of serious relationship and that's not what I'm about, you know what I mean?'
"Definitely..." I said.
Up to that point she was looking at her glass. Then she looked up and stared at me. She sort of realized she maybe had crossed the line.
"How old are you, anyway? Early 20s?" This was the first time that looking older than my actual age made me really happy. Before I could answer (I'm not a good liar), she kept on going.
"I miss those college days...you could fuck anyone and not be in a relationship. You know, just good wholesome fucking, you know what I mean?"
"Of course. I totally understand where you're coming from". At that point, she leaned over and saw my fucking huge boner, which was almost stretching open my shorts.
"So, at what time do you have to get back?" I said, erotically.
"5 PM." She acted as if nothing ever happened.
"Hey, like you said earlier, I could show you around the house" She told me she was looking into buying a townhouse. I gave her a quick tour, making sure we would end up in the basement, where our big futon is located, which I judged would be an excellent place to fuck. During the whole tour she was definitely flirting, and it was getting more and more obvious that we were gonna have sex. When we got to the basement, I kissed her. "Ohh...so you're a romantic, uh?". I knew how to get it on, given the fact that I had seen at least 100 full-length MILF movies in the past year. We made out for a while, I slowly pushed her on the futon, and then I started moving down. She took off her top and bra, and her tits looked 10 times better in real life because she wore a cheap bra. "You weren't expecting that, uh?" she said, looking at the pleasantly surprised look on my face. "I can't fucking believe it" I replied, and I thought that my dream was finally becoming reality. I thought it would take me years to first have sex, and I never would have though the first time would have been with someone as hot as her. Seing her body naked and having her feel up my cock was better than I would have ever though it would be like. In a mere 30 seconds, we were both naked and she was giving me a blowjob, which I still recal today as one of the best blowjobs I've ever had. Her sweet lips and tongue rubbed themselves so well against my young penis, and she moaned already, and saying stuff occassionally like "I didn't think it'd be that big" and "I can't wait to fuck..." The second time she said that I said "Are you ready?" to which she slowly "Fuck yeah...". Everything was going extremely well, but I was still wondering why a hot woman like that would want to fuck a low-life like me. Maybe I had too low self-esteem or maybe girls that age would do anything to fuck. It was one or the other, possibly both.
I'll never forget the first stroke I took in her pussy. Our sex was unprotected, by the way, because oftentimes when she blew me she said "I can't wait to get all that hot cum in my face". This is when she started to moan like a beast. I was happy the neighbours weren't home also (remember, I lived in a townhouse). "Fuck... oh yeah....oh oh... put that cock as fucking deep as you can in my slutty 36 year old pussy right now" were some of the most common expressions she used. We did it for long, and in almost every position. I was always focusin on not getting my cum out, which was extremely hard to do. I was now having sex with a woman who, 30 minutes earlier, looked like an innocent every day mom who was taking care of her kids. Now, we were both fucking like there was no tomorrow, we mainly did anal and normal sex. Her asshole was already stretched, which I later learned that she had a pretty active sexual life, and that she liked to fuck anal. After about 30 minutes of exquisite sex, I said "Are you ready to get all that white shit in your face?" to which she replied "Yessss". She got on her knees, and then the best feeling in the world came about me. All that cum spread all over her face, from her nose to her chin, and she swallowed a part of it, and finally said "You fuck good". She went to take a shower, and after that we chatted for about 15 minutes before she left to do her shopping. She gave me her number because she wanted to 'meet up' again in the future, and before she left she whispered "Don't tell anybody" and gave me a sweet, cute, and innocent smile. At that point, she was back to Michelle, the 36-year-old single mother who had 3 kids and a busy lifestyle. But, for 30 minutes that day, she was someone else, a slutty nymph chick who liked recieving cum all over her face.
I still know Michelle to this day. We started meeting each other every few months, for sex and just for chatting. I told her a couple of years ago my actual age, and she wasn't the least bit surprised, and she said that she knew I wouldn't tell anyone about our little secret. She could tell I was a virgin and it was my first time, and she even gives me sex tips once in a while. Her kids and herself are older now, but she's still incredibly hot. I've even gotten to meet her 3 kids, and I go out with her without sex once in a while. We go to a café and we just chat, we're good friends. When people ask me how I met my 42 year old friend Michelle, I tell them we met a couple of years ago, on a wednesday, when she came knocking to my door because her ill son needed medical assistance. I still haven't told anybody about our little secret. Neither has she. This is how I met my Milf fuck-friend.
