[M]y [F]irst Cougar Lead to Other Firsts

Aunt Kim was not actually related to me. She was my best friend Mark’s Aunt, actually. However, Mark and I were friends from preschool through adulthood, lived 4 houses apart, our parents were friends, we were together all the time and Kim was always around. So, I called her Aunt Kim.

She was quite a bit younger than our parents and the other adults that were around and she wasn’t married and didn’t have kids of her own. So, she was the coolest adult I knew, by far. As a kid, I knew that she was pretty and loved being around her. She was always perky and positive and energetic. She acted like a kid around the kids, but could then hang with the adults and even help to smooth things over for us if we got into trouble.

As I got to be 12 or 13 and interested in girls, I noticed that Kim was not just pretty and fun. She was smoking hot. Really active and fit, often wearing workout clothes. Kim is about average height, shorter black hair, big brown eyes, usually very tan, medium size perky tits. Compared to the other adults I knew, she was so well put together. Nails always manicured, makeup looking perfect, smelling fantastic. At this point, she was about in her mid-late 20s, but still loved to hang around with us, playing basketball or tag or other goofy games. Any little accidental bump or touch from her was magical for me at that age.

By the time I was high school age, I realized that kim was a bit of a party girl. I’d overhear bits and pieces of her conversations with the other adults, mentioning “so many shots” or “he wouldn’t leave”, things like that. Still, she was really comfortable hanging with the kids, watching movies, asking us about girls at school, giving us advice about dating, sex, drinking, how to deal with different social situations, etc. All of her advice was spot-on and it was fantastic. We got all of the experience and knowledge of an adult with no judgment of uncomfortable conversations. She never told us anything about her own exploits, but it was pretty clear that she knew her way around. She was still hot as hell and hearing her talk about sex was an incredible turn-on, but it also felt like the world’s biggest tease. For a multitude of reasons, I would never have a chance to be with her. It might have been a fantasy somewhere in the back of my mind, but I never even considered if / how it could happen in real life.

Fast-forward a bit and Mark and I go away to college at different schools. So, instead of seeing Kim several times per week, I get to see her only a handful of times per year, maybe at holidays and a summer BBQ or two. She is still hot as hell, but my obsession with her wanes a bit. I am doing okay with girls my own age (ironically, some of that is due to some of the advice that she had given us in high school) and our conversations are a little more awkward than they had been before. After college, Mark and I both get jobs back in our hometown and get an apartment together in the city. We don’t live too far from Kim and start to see her more often. At this point, we are in our early 20s and she is mid-30s or so. She has us over for dinner a couple of times per month, we go to concerts and festivals together, we get to know her friends and she gets to know ours. While she still gives us tips on the neighborhood and things like that, we are all adults at this point and our relationship and conversations evolve accordingly. Still, any notion of getting together with her at this point is completely gone from my mind.

One Thursday evening, Mark and I and Kim had made plans to meet after work for drinks and dinner. Kim showed up wearing a white blouse with a couple of buttons undone at the top, a mid-length blue skirt and heels. She looked professional, but also hot as hell. I was used to seeing her on the weekend in workout clothes or jeans. We had a dinner and drinks and laughed a lot. As we were paying the bill, Mark noticed a girl across the bar who he had been on and off with, but who had been avoiding him lately. Kim encouraged him to go talk to her, which he did. Kim and I went to the bar to continue drinking, leaving our table for other diners. We were both feeling good as we continued drinking and laughing. The bar was getting crowded and we were getting jostled and smushed together quite a bit. I figured it was just my imagination, but it seemed like Kim was enjoying it, giggling and letting her hands and body linger a bit longer than necessary when we touched. Mark came over to tell us that he was leaving with his girl and we wished him well. That lead Kim and I to a discussion about Mark being a lucky bastard and complaints about how we were both in the midst of dry spells in the sex department. At one point, she commented “seems like a couple of pals could help each other out.” I smiled and nodded, but had no idea what she meant. Did she mean that Mark should be helping me get laid? Did she mean that she and I were the pals who should be helping each other? Did she mean that we should be setting each other up with friends? Did she possibly mean that she and I should fuck? She said it completely deadpanned with no intonation to indicate that she was suggesting something naughty and no grin or smile of any kind. We had another drink or two, talked about other topics and then decided it was getting late and we should leave.

My apartment was just a couple of blocks from the bar and hers was another couple of blocks beyond that, in the same direction. So, we walked together. As we approached my place, I got nervous about how this evening was going to wrap up. I wanted her to know that I was certainly interested in helping her out, if that was what she had really suggested. Then again, if I had misread the situation, I didn’t want to make a complete ass of myself. I decided to go with a trick from her book and asked “you wanna come in?” in a totally neutral tone without even looking at her, forcing her to make a call on what I might have in mind. At this point, we were standing close at the apartment door and I was fumbling with my keys. “You fucking know I do” she growled and we both leaned closer for a passionate kiss. My mind was racing with years of lust and teenage fantasies about to be fulfilled and my cock started to harden accordingly just as she reached her hand to my crotch for a feel.

I somehow managed to get the door open and we stumbled inside onto the couch, making out the whole time. I started to grope her firm tits, when she pushed me back and told me to get a condom. I did as I was told, hurrying over to my bedroom to get one from the bedside table. I couldn’t have been gone more than 15-20 seconds, but she had already shed her blouse and bra and was stepping out of her skirt and underwear as I approached her. She looked even better than I had imagined all these years. Tight, tan, flawless body, firm tits, perfectly round little nipples with pencil eraser nipples and a neat little patch of dark pubic hair. I still could not believe that this was happening and wanted to take it slow to savor every moment. She had other ideas. As she stepped out of her skirt (still wearing her heels), I leaned in to continue our kiss, but she reached out and put a hand on my shoulder to stop me and push me down toward the floor. When I was sitting on the floor, my back against the couch, she moved her hand from my shoulder to the back of my head and pulled me toward her pussy as she stepped closer to me, putting her right foot up on the couch to provide wider access.

There were no playful kisses or teasing licks happening here. She was immediately grinding her pussy on my face, ordering me to “fuck me with your tongue”. My mind was racing. Partly because I had thought about doing this with Kim for 10+ years, but also because this level of assertiveness and sexual confidence was new to me. I had been with maybe 7 or 8 women up to this point, all of them college-age girls. Just like I’m sure I was, they were figuring out their sexual style, preferences, etc as they went along and might have been a little hesitant to try new things or do things outside of the standard playbook or vocalize what they really wanted. After a bit, Kim used her hand and her voice to direct me to focus on her clit, still pulling me hard against her, moaning with increasing intensity, until she pushed me away, telling me “get your clothes off, I need to cum on your cock”.

She helped pull me to my feet and as I took off my shirt and undid my belt and pants, she stood in place, one hand on my hip the other feverishly fingering her own pussy, keeping herself on the brink of orgasm. Again, my mind was racing as I had never been with someone so confident, so accountable for her own pleasure. I guess she could tell what I was thinking, as she smiled wickedly and asked “Do you like that? Do you like how I have to touch my pussy when I think about your cock?” I was in some type of sexual fugue at this point and have no idea if / how I even responded. Probably just nodded my head like a moron.

As I pushed my pants to the floor, she pushed me down onto the couch and straddled me, her hot wet pussy hovering inches above my hard dick. “C’mon, put it on”, she said and I realized that I was still holding the condom in my hand. I tore open the package and rolled it on, Kim sinking her pussy onto the tip of my cock before the condom was even at the base. She started bouncing hard, leaning forward to kiss me and then guide my mouth to her tits. This lasted for only a minute or two before she cried “I’m cumming!”, increasing the intensity of her thrusts, before stopping entirely, settling down on the full length of my cock while she panted on my shoulder. She sat upright again, a big beautiful smile on her face and said “Holy shit, that felt so good. You have no idea how much I needed that.”

“How about you? Are you gonna cum for me?” she asked as she started riding me again. She reached around behind her back and fondled my balls. I realized that I wasn’t really doing my part in the dirty talk department, so I joined in. “Yeah, I’m gonna cum so hard. Your tight pussy feels so good.” She smiled. “Oh yeah, you like this 35-year old pussy? You like me touching your big, full balls? You gonna unload those balls for me?” This went on for a while, but I wasn’t close to cumming at all. It must have been a combination of the booze and the sense of disbelief that this was actually happening. I decided to take some control of the situation and pushed her off of my dick, then skooched out from under her and arranged her on the couch so that I could stand behind her. I lined my cock up with her pussy and she backed herself onto it. However, I was determined to control at least this part of the encounter. I leaned into her hard, pushing her into the couch so that she could not push back and I could control the rhythm. She loved it, gasping as I pounded her, reaching down to play with her clit and telling me that she was going to cum again. She got quiet as she came, then moved her hand from her clit to my balls, asking if I was going to cum. “Aren’t you going to cum for Aunt Kim?” She was pulling out all the stops. I hadn’t called her “Aunt” in many years, but she knew that would make it sound extra naughty. Unfortunately, I wasn’t close and told her that we can stop and take a break for a while. I took a step back and my cock pulled out of her creamy pussy with a “pop” sound before I tore off the condom.

Kim rolled over onto her side and laid motionless on the couch for a moment. I have to admit, I stood there with my hard, wet cock and felt pretty fucking proud of myself as I looked at this beautiful fantasy woman laying in a quivering wet mess on my couch. But she was not one to back down from a challenge and sat up on the couch and reached for my cock, pulling it to her mouth. She alternated between deep throating me and licking and flicking the head with her tongue while stroking the shaft with her hand. After several minutes, she took a break, looking up and asking if I was going to give her my cum while propping my foot up next to her on the couch so that she could better access my balls and, unknown to me at this point, asshole.

She gently took my balls into her mouth, one at a time, nuzzling and licking them while reaching between my legs to place her middle finger on my asshole. Again, this was something new to me and I must have jumped (or clenched, or both). Kim pulled her finger away and asked “Oh, you don’t like?” as she moved her mouth from my balls to the head of my cock. I just gave her a shrug and she said “well, you’ve got to at least try.” This time, she she reached down to lubricate her finger with her own pussy and put it back on my asshole, telling me to just relax as she slowly wriggled it in, deepthroating my cock at the same time. The combination of these 2 sensations took me from 0 to 100 almost instantly as I suddenly felt my balls tingling and my asshole contracted on her finger and I came about as hard as I ever had in my life straight down Kim’s throat. She slowly took me out of her mouth, pausing to lick and suckle several times along the way.

I was light-headed at this point and flopped down on the couch net to her. She leaned into me and we chatted a bit, agreeing that “helping each other out” had worked out pretty well and we had both gotten just what we needed. Because of our age difference and history, we both knew that sex was not going to lead to some type or romantic entanglement or relationship. That helped us to compartmentalize it and treat it purely as a physical release (we ended up doing this several times). I also think that Kim enjoyed the fact that she was introducing me to new things sexually and it felt like a natural progression from when she had been a teacher and mentor to us.

Like most of my stories, this one ended up longer than I expected, but I hope you enjoyed reading it. There are more Aunt Kim stories if anybody is interested. Thanks!

Source: reddit.com/r/gonewildstories/comments/l5nt1r/my_first_cougar_lead_to_other_firsts