My Current Wife Used to be a Cougar, Liked Younger Guys and Prior to us Dating, I Used to Date her Daughter.

Changing names for privacy. When I was 25 yrs old, I met “Alicia” on AOL chat. She was 19 at the time, we got to chatting daily. Then we met. She had brown, straight, shoulder-length hair (still does, actually) wore large glasses, short, petite. A stereotypical cute, nerdy girl with a tongue ring. We had sex on our first date. I went down on her shaved pussy then we performed missionary, and I pulled out, nutting on her stomach, filling up her belly button. After that, it was pretty much game on and we became a couple. I soon discovered that I enjoyed her tongue ring during oral sex. It was just a ball shape on top of her tongue and man that thing did some wonders. She would play with my cum in her mouth before eventually swallowing, sometimes jokingly threatening to “snowball” me. (spit my own cum in my mouth) but she never did, and I wasn't into that sort of thing then.

At some point, she introduced me to her 36 yr old mother, "Kara". A redhead with shoulder-length perm cut. Standing 5'1" tall with green eyes, nerdy glasses and petite figure just like her daughter but with larger breasts and a thicc ghetto booty. I mean, her booty was nice, the kind that bubbled out so far that you could probably set a 6 pack of beer on top of her butt cheeks behind her back, and they'd hold up without tipping over. I learned from "Alicia" that she was born when her mom was like 17 and her dad was only 14 at the time, and that she has always dated younger guys. I didn't know the term “cougar” then, nor put much thought into it. Alicia and I had a couple of pregnancy scares, probably because our whole relationship was mostly based on sex. That's pretty much all we did with our free time together. We would often have sex on my couch, take a nap, then wake up and do it again. After a while, she decided that she wanted to move on. That, perhaps us, as a couple, just wasn't meant to be. So we opted to remain as good friends.

Christmas later that year came by and "Alicia" invited me to come over to her moms house and enjoy the holidays with them because I was just living by myself in a rented mobile home and had nothing going on. So I thought might as well and stopped over. Her mom knew that we had separated, but still treated me like one of the family. We ate dinner and later that night we all sat around and watched movies together. By around 11 pm, It was down to just me, "Alicia" and her mom. "Alicia" wanted to head back home and I remained just to finish out that particular movie. I don't even remember what it was. So she left and I had intended on leaving after the movie was over. Before the movie ended, "Kara" had complained that her feet were cold and wanted to shove her feet behind my back to warm them up. When the movie ended, she sat up, I don't remember what if any conversation took place at that point. All I can remember is her leaning over to me, and we began kissing. Naturally that got my hands feeling a need to explore and began messaging and groping her breasts. She whispered in my ear "I wanna fuck you" and I was like holy shit. I remember replying as "I want you too" or something similar. 

She led me into a bedroom, not hers, but perhaps a guest room. She told me to get undressed and she'd be back. She went to the bathroom and came out just wearing a night shirt or long T-shirt. "You ready?" she asked, she wasn't messing around. I was still hard, so she climbed over top of me and I quickly felt the familiar warm, wet sensation as I slid inside her pussy. She took her shirt off and revealed a pair of torpedo shaped titties. Perky and poking straight out as if ready to launch. Her areolas and nipples were very light, almost the same shade as her skin, with a slight pinkish hue. Freckles adorned her chest just above them. She began riding me in cowgirl position, and at some point I realized that she fucks a little different than her daughter. Instead of just riding up and down when on top like "Alicia" did, she would also work her hips in a twerking like fashion, all while squeezing her vaginal muscles rhythmically. It felt like her pussy was literally trying to suck the cum right out of my balls. She could tell when I was almost there, then she would stop and wait for my urge to settle back down before performing tantric sex by just squeezing her vaginal muscles in a rhythmic fashion. Then she'd start riding again, twerking that thicc ass as I groped her cheeks and held on for the ride. She kept repeating it, not letting me cum yet, even giggling about teasing me which at this point was almost torture. I began to beg and plead with her to let me cum and, with sadistic giggling, seemed to enjoy letting me get almost there before stopping. After what felt like an hour, she finally let me cum, saying "stay inside". I'll never forget her saying that as she expertly worked her hips and vaginal muscles while I shot out every drop I could muster. 

From then on we began dating. We eventually had to tell "Alicia" and "Kara" had a private mother/daughter talk with her. I don't know what was said exactly, but I'm sure she had to explain some things. “Alicia” was shocked but took it better than I was figuring. She thought it was a little weird for a while but warmed up to it. Her mom and I then moved in together for a couple of years or so before we decided to get married. "Alicia" had just got engaged too, and I don't know why exactly, but her and I were alone one evening just talking about stuff and for whatever reason we thought it would be a fun idea to have sex one last time before we got married. So we did, I knocked on off inside her for old time's sake and watched my cum ooze out of her afterwards. Honestly, it was probably the hottest, best sex her and I ever had together. Probably because we were doing something that we weren't supposed to, but we figured we did it many times before, so one last time wouldn't matter much. That was the only time that either of us had cheated on our significant other. Then I married her mom in Gatlinburg, Tennessee, and we've been married for about 13 years now and Alicia and her husband has been for about 12 years and had a daughter together. Occasionally whenever "Alicia" comes over, I'll look at her and her mom together and think to myself about how I've managed to fuck both of them and how awesome it would be to have a threesome with them, but I know that'll never happen. In comparison, I'd say "Alicia" gave better blowjobs, but her mom is much better at intercourse.