Category: MILF Sex Stories

I (35 now) had met my wife (32 now) at a camp we were both counselors at back in 2009 and we developed a summer relationship. It was a very physical relationship (which you can read about in another post) but we both knew we would be going back to different colleges for the fall. She attended Liberty University and I was at a smaller college about 4 hours away. We would meet up on most weekends. She’d visit me or I’d go to see her and even sometimes we would meet in the middle. All of these visits consisted of a lot of sex.

I was 22 years old, the restaurant manager of a local spot. My best waitress was Susan, a 38 year old struggling single mother. She worked as much and as hard as she could to give herself a decent life, but she always needed help. She was raised by an abusive father and absent mother, she never learned to do math or drive a car etc. She didn’t need to do much math here so that was okay, and I was happy to give her a ride home everyday in return for how hard she worked, not to mention she lived on my route home so it added maybe 2 minutes to my drive.

Susan wasn’t drop dead gorgeous, but she did have a pretty face, beautiful straight, dark brown hair and very light freckles. I can’t forget to mention her abnormally large ass and thighs, it honestly could’ve been a medical condition. It wasn’t off putting at all, but it definitely didn’t fit her shorter, thin torso and C cup tits. Susan flirted with me quite a bit, but I always brushed it off, I wasn’t super into older ladies. I did fantasize about her a few times when I was particularly horny though. So the night she offered for me to come inside, I did exactly that.

One of my best friend’s mothers is about 42 or 43 years old and is absolutely gorgeous. She is about 5′ 7″, with long, smooth legs, and perfect breasts that are not too big not too small. They are natural looking, so they look perfect. She is the typical blonde stacked soccer mom who everyone wants to fuck in the neighborhood. She is a gardener and takes extra care of her bushes in front of her house and her gardens in the backyard.

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I’m a single, divorced mother who has an 18 year old son, his best friend Tyler (not his real name) is 19 and quite a handsome young man. Now this goes back about a week. Tyler came over to visit my son and hang out for the day and I was in kitchen getting lunch ready. Tyler came down stairs to get a drink and we had short chat. During the chat I could swear he was checking me out by looking at me up and down but at the time I didn’t think anything of it so I put it out of my mind.

2 days go by and Tyler stops by again but doesn’t stay long as he and my son went were heading out for the day. We were in the front room as I was cleaning it and he was sitting on the couch waiting for my son. Now I must admit what I did next was on purpose as I wanted to see if I was right or not about the other day. I went to the coffee table and started to clean it. I had bent down in front of Tyler in a way so he could see down my top, and lo and behold he was staring right down it. When I rose up he quickly looked away. I didn’t say anything as I didn’t want to embarrass him. I should’ve been mad but I was quite flattered that someone as young as him still found me attractive.

Shortly after we got married, I met my then husband’s ex at a reunion. They had broken up very amicably. After talking for a bit, we invited her out for dinner as she would be in town for the next day. The dinner went great, and we had a lot of fun. Afterwards, we went home for more drinking, and during the conversation that followed, the talk turned to sex. She told me I was very lucky to be married to him. She told me some of the fun stuff they had done, and I told her about things we had done. My husband just sat there feeling very proud of himself.

About six months ago we had our twin daughters and sex has kind of been on the back burner, but last Valentines Day i gave my husband a sex coupon book that included a few coupons for his favorite things and a few for things that were kinkier than normal for us.

Today, my amazing MIL offered to watch the girls for the night so we could go enjoy the new Dr. Strange movie like real grown ups. After dropping off the girls we come home to get ready for our date afternoon when hubs tells me “Wear something easy access” and hands me a coupon for 1 full day of free use. We’ve never done free use before, but the idea was definitely exciting.

I went back to my hometown for my college’s spring break. A lot of my friends went to the beach but i wanted to go home for the week and see my family. (Little did I know what this week would turn into!)

On my first morning being home I decided to visit my favorite bagel shop because at school the bagels were not the same. I walk into the store and standing at the counter paying for her bagels is Mrs. Jackson. Or just Tasha as I would learn later. 5’3 brunette with amazing curves. I couldn’t believe how good both her tits and ass looked for her age. Mrs. Jackson was the mom of my childhood friend Daniel. I was friends with Daniel throughout elementary school and high school but we haven’t talked since we left for college. Our mothers are still friends though.

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