It’s funny, now that I’m 39, I tend to fantasize about younger women. But when I was young, I had a huge cougar/MILF fantasy. This is the story of the hottest time I indulged it.
I was 24 and temporarily in the Washington, D.C. area for a few months. I was in the military, then (and still now) a 6’4″ corn-fed ex-jock who grew up on a farm in the midwest, with broad shoulders and a reasonably built body, even if I don’t exactly have the muscle definition of Michelangelo’s David.
I overheard an acquaintance at a party describe the Capital Grille in downtown D.C. as a “cougar bar,” and that was all I needed to know. I headed there the next Thursday solo, trying to play up my simple-minded young jock vibe with a tight-fitting white polo shirt. I sidled up to the bar, ordered the cheapest draft they had (maybe Yuengling?) and started looking around. The after-work crowd filtered in and out for an hour or so, and then I saw her. A 45-year old blonde dressed in a sleek black dress that was somewhere in between “work” and “cocktail.” Tits pushed to a level where they were clearly intended to draw attention.
She ordered a drink near me and I deliberately tried to paint myself as “not from here and in need of guidance” by asking about how crowded the bar usually is. Hey, playing the dumb blonde doesn’t only work for women. We chatted for a few minutes, I learned that her name was Jane, she smiled at me enough to give me hope, and then re-joined her friends. But before I left, I managed to score her number, and we made a date for the next week.
Our “date” was at a cocktail bar. This was the early heyday of the speakeasy thing. And she showed up a smokeshow. Sort of wearing that high-waisted jeans and bodysuit top look. Just the way she dressed told me that we were headed the direction I wanted things to go. The “date” was actually pretty nice with good conversation. She made a couple of “oh, gosh, you’re so young” comments at things I said, but for the most part, the age difference didn’t come up. (I didn’t notice, but wonder how it looked to people at other tables. I looked every bit the part of a young-20s wet-behind-the-ears military bro, and although she looked hot, there was no mistaking that she was quite a bit older.)
But enough chit chat about the chit chat, two cocktails later and a check that she wouldn’t let me pay (ugh, my masculinity!), we were headed to her apartment.
Holy shit, her apartment. She was a partner at some law firm in D.C. She had told me over drinks that she had been married, but because she worked like 80 hours a week, her marriage broke up and she never had any kids. So I guess that’s where the money for this apartment came from. But damn, at that time in my life, I just didn’t know that people–certainly not people I would interact with–had apartments like this. To simple old me, it was like from a TV show. Like it could have been Frasier Crane’s apartment or something. It just felt “rich,” with these dim lights and Pottery Barn furniture and actual art on the walls. After a glass of wine on her couch we were making out. After a second glass, she was pawing my increasingly throbbing crotch and taking my hand, pulling me toward the bedroom.
As I climbed onto the bed, she excused herself to the bathroom. Sort of not knowing what to do, I took my shirt off and propped myself up on the pillows, thinking I was pretty suave. When the door opened again, she was in lingerie. God damn, my weakness. This cougar came to play. And believe me when I say that she took the lead at first. She fucking jumped me on the bed, and had my pants off within what felt like seconds.
She stroked my cock but didn’t suck it, and I flipped her over to give some attention to her tits, still in this beautiful black lingerie bra. She was probably about a 34C, and this bra was framing and accentuating them just perfectly. After burying my face in her cleavage for a while, I straddled her and toyed with my dick in between her tits. It wasn’t quite a full-blown “titty fuck” but it was trending that direction. I was mesmerized by both the lingerie and just the idea of this woman two decades my senior moaning as I took charge.
After making out and rolling around a bit, she whispered, “I’m so wet,” and I reached my hand down inside of her black panties. She was wet, alright. I started gently exploring her pussy lips and clit with my hands, my mouth and tongue alternating between her neck and her still-in-bra tits, and she moaned a bit and smirked, “I didn’t expect someone like you to be so good at foreplay.”
I could tell she wanted me to play a part. I was game as hell for that, but too young and dumb to do anything other than play it really obviously. “Well, I aim to please, ma’am,” I said with a goofy overgrown puppy grin, and she laughed. She said, “well, I don’t think I need any more foreplay, Mr. Army Boy” (I’ve never forgotten how she used that phrase). She started to maneuver out of her panties but I said, “nuh uh.” She looked at me quizzicly for a second and I pushed them to the side, now finger fucking her more aggressively. “They can stay on.” She nodded in response.
My jeans were within reach and I reached over to grab a condom out of the back pocket. She arched an eyebrow. “They teach us safe sex in the army,” I said in response. “Oh, do they?” she laughed. “Well, or at least to always be prepared.” “I thought that was the boy scouts.” “Well, they didn’t teach me what I’m about to do in the boy scouts.” (Solid banter, bro, I thought to myself proudly!) She tried to sit up a little to help me put the condom on, but it was my turn to be more aggressive. I gently pushed her back down to unfurl it myself as I loomed over her.
Once I had it on, I shoved the panties aside again, and started to enter her in missionary. Despite being wet, it took a few short tip-thrusts to get down to business, and by the time I was all the way in, she had brought her legs up over my shoulders. “Fuck that’s deep,” she said, and as I started thrusting, I had the presence of mind to burn the image in front of me into my mind. Here was this cougar, still in bra and panties, some powerful D.C. law/lobbyist lady, and I was her one-night-stand conquest of a young buck. I don’t know which of us felt more of an achievement.
We both started talking increasingly dirty (something that always came naturally to me even when I was young), and while I’d love to say we changed to a ton of different positions and lasted for hours, this fuck was pretty fast and ended in the same position where it started. When she came, she insisted that I not move, just holding my dick deep inside her, letting me feel her writhe on it. After she came, I picked up the pace to bust my own nut, and it felt like one hell of an orgasm.
After catching our breath, she said, “can I please take my bra off now?” I laughed and said of course. As her tits spilled out, I started sucking them again with reckless abandon. That ebbed and we cuddled a bit more, talking and having another glass of wine in her bed.
A bit later, now well into the wee hours of the morning, she had stroked me hard again. She reached into the nightstand for some lube and straddled me, sliding her slit along my cock. “I don’t have another condom,” I whispered. She looked genuinely disappointed and said, “fuck.” The thought that I was about to lose out on a second round with the cougar drove me to panic. I was literally on the verge of getting up and digging my used condom out of the trash and, uhhh, “recycling” it when she bit her lip and said, “no, it’s okay, I think it’s okay. I mean, I’m on birth control, obviously. It’s just…it’s ok.”
And with that, she slid along my dick a bit more and then just…sat down on it. With her on top, there was a lot less moving, she was just moaning like no tomorrow grinding and writhing on my hard dick while I played with her tits. I think I was smiling like a doofus not knowing what to do, but her eyes were rolled back and closed as she just enjoyed gripping this human dildo inside of her.
After she came–quite quickly, and none too quietly–I then got mine from an extended doggy session. In that position, her ass looked amazing. My only faux pas was letting my fingers graze close to her asshole at one point. She glanced back at me seriously and said, “no, no. Not for me.” But she clearly didn’t mind me continuing to thrust, and between her ass and the bareback sensation, I didn’t last much longer.
We fell asleep with her hands gently tracing my then-decent pecs (ahh, youth), telling each other how amazing it had been and how we should do it again. I woke up to the smell of coffee. She was dressed in a short robe, and we were mildly flirtatious, but I felt like the morning light had brought some distance between us. It was clearly time to go, and we probably both knew this was going to be the end of the story, even though we both professed otherwise. “Keep in touch, ok?” she said as we kissed on her doorstep, but we never spoke again.
Still, I google her every once in a while. She’s still a lawyer at her firm, probably still in that big, rich apartment. I wonder if she still chases younger guys. Judging by her website portrait, she has certainly gotten older, but definitely still in the category of “looks great for her age.” I’m tempted to send her a note every time I look her up, asking if she remembers the young military officer from the Capital Grille. But I never do. The memory of hunting this cougar is enough for me.
Source: reddit.com/r/gonewildstories/comments/tcsvli/the_young_army_officer_in_the_big_city_bagging_my
Great story, you should write more.