I posted this on r/cougarsandcubs to celebrate the uniqueness and differences between the women us younger men love and enjoy while also sharing my own unique taste and appreciation for the women I have had the pleasure of getting to know. This is the uncensored version. The first time meeting a woman is exciting. The smell and touch of a woman is just magical. For some reason, meeting a woman older than myself for the first time is an even more surreal and almost out-of-body experience. The nerves of anticipation, the first eye contact and then touch, the path of the conversation, the initial physical intimacy, the exploration, the syncing of body and mind, and on and on.
Background: A long-term relationship I was in with a woman my age ended mutually last spring. After some self-reflection, I decided I would fully pursue my long-time attraction to women older than myself. I had briefly attempted it as a 20 year old with no luck. I was now in my late 20s and had filled out physically. My personality had also matured with life experience leading to a boost in confidence and intuition to carry on a conversation with most any sane human. It took a month or so to figure out my approach, but I was ready.
My personal taste in women: I tend to be most physically attracted to women between 45 and 65 years of age. Curves also catch my eye, but, more specifically, the curves of a typical woman you’d see at the office or grocery store and not the stereotypical Hollywood cougar/milf. I also tend to go for pale or fair-skinned women. Redheads are my weakness. Redheads with curves are my kryptonite. I am typically turned off by women that are interested in coming over or having me over almost immediately. It is a red flag, but I have succumbed in a moment of weakness. I enjoy the back and forth and, to put it bluntly, the pursuit. All five older women I have been with intimately had never been with a much younger man before our time together.
The Uniqueness of Women: I have met all of these women on what I would call traditional dating sites. Now for the women (after a short about me). I will format each description with age at the time of first meeting, appearance, how we finally met, more on her appearance, more on our first meeting, her uniqueness, and how long we saw each other.
About me: Live in a larger city, light brown hair and brown eyes, 6’3″, 200 pounds, baby-ish face so I typically keep some scruff, athletic build but not ripped.
The First, 53 years old: Medium length brown hair, blue eyes, 5’4″, pale-ish skin, hourglass figure. She always dressed casually when we met, but the jeans and tops she wore fit very well and accentuated her form simultaneously leaving less to the imagination while also causing the imagination to work much more. She has the proportional curves of the women I grew up watching on My Friend’s Hot Mom by Naughty America. It was too good to be true. We chatted for a couple weeks online before finally deciding to meet at a park after work one day. We both had lots of anxious jitters and the walk and talk assuaged these slowly. This led to a bench, her car, some teasing, and a decision for me to come over the next night. The fantasy became a reality the next night. She was the dream come true. After some conversation on her back porch over some Mike’s Hard I suggested we take it inside. In the kitchen she began rinsing out the bottles to be recycled and I saw my chance. Hands on her shoulders and some pecks on the neck and we were off. She soon guided me to her bedroom and left me, both of us still fully clothed, to freshen up in the bathroom. Five minutes felt like forever as I waited on the bed, now down to my briefs and trying to strike a playfully sexy pose. She came out wearing much less than she had on going in. D cup (estimated) with average size areolas and pink eraser-tip nipples that stuck out a half-inch, wide hips and proportionally curvy butt, well done and subtle tummy tuck, and a pleasantly surprising and very inviting landing strip to her treasure. She has the type of body that looked spectacular in every possible position we got into. The intimacy couldn’t have gone better. I have found my body react in different ways during the first time with a woman. Sometimes I have the endurance of a god. This may be due to the nerves or maybe some primal instinct to satisfy a new mate as well as possible. The single beverage may have worked to loosen me up just enough though, and, even with protection, after 5 slow, sensual minutes inside I was close. Thankfully she was too and her pulses started just before mine and sent me over. We went up and came down together. One more rougher round later and we agreed I should stay the night. I was glad I did as she woke me up the next morning with her mouth around me. She’s the first and only woman that’s ever done that for me. Then she served me breakfast. I was hooked on older women. I learned she was recently divorced and, in future meetings, she would take verbal shots at her not present ex-husband during intimate and not intimate times. It was odd at first, but grew on me. We met up four more times over the next two months, but I dropped contact with her after she brought up something she was into that I just could not stomach (nothing illegal, but I’m not going to give any other details).
The Cheater, 47 years old: Shoulder length blonde hair, blue eyes, 5’8″ (estimated), pale skin, big body in a great way. We had only been chatting for a couple days which breaks my rule of getting to know a woman before meeting. This should have been a sign, but I wasn’t thinking as rationally at the time. It was late and we were messaging about naughtier things. I lamented us not being in the same place. She sent her address right over and suggested we change that. Again, red flag. I was caught off guard. I didn’t have protection at the time and it was too late to pick some up, but she was fine with just being handsy with each other so I was on my way. Nice apartment complex. I didn’t notice any signs of a man in her apartment, but wasn’t really looking either. We sat on the couch while something terribly boring played on the TV, reminded me of UPN or something. The boredom of the program may have been intentional on her part. Slowly inching closer, teasing more and more, my hands massaging her shoulders and back. I suggested a more suitable place to give her a proper rub down. Off to the bedroom. She laid down on her stomach, more massaging, removing her shirt for better access, unclasping her bra for better access, removing her bra for better access, and then it was time to rub down the front. She rolled over: D cup (estimated) with light pink almost ghost nipples, round belly that didn’t hang over at all when she stood up, flat butt, and I would later find her completely bare downstairs. Her nipples were very unique and so much fun to play with. When I first uncovered them they were almost inverted, but came out to play once excited. Not sure if that’s common, but it was my first experience with a woman blessed with them. I explored all over with my hands and then with a vibrator all while telling her dirty things. She was amazing to please and watch. When she was building to and going over the edge her face and cleavage would get redder than a stop sign. So sexy to see and know you helped get her there. She could release over and over and over again. I lost count, but got spankbank views from all different angles. The sheets were soaked in several spots by the end. She said it was my turn, got out some lube, and tugged everything out of me. It was past 3 AM at this point so we agreed to more soon, and I left. I checked in the next afternoon and got a response later that night that she was in a relationship and guilt-ridden. Poor guy. I didn’t feel the need to respond.
The Biker, 52 years old: Shoulder length brown hair that she typically wore in a pony tail (until I let it down), green eyes, 5’4″ (estimated). Tan where the sun hits and, I would find out, pale everywhere else. I only ever saw her in (or out of) bejeweled and faded jeans and female versions of affliction type shirts that did their best to contain her bust (to no avail) so the sun only hit her face, arms, and the little cleavage she bared publicly. Multiple pictures on her profile with her bike. This is normally not my type, but the body and her intelligently dry personality was. She was one of a handful of women that would humor my online advances, but that I never thought would take me up on them. Our back and forths were enjoyable and playful, but almost always shorter than they were with other women. She is to the point. We chatted for months and it probably amounted to less than the conversations had between me and other women in a week. Patience paid off in this case. She messaged back quickly and we chatted continuously throughout the day. Her high school aged daughter was off to visit her (the daughter’s) father out of state for Thanksgiving. She wanted to meet for lunch on Saturday. We audibled to an earlier coffee the morning of. The coffee was a bad choice for jitters, but I made it to her house. I sat on her giant L couch in the high-ceilinged living area as she grabbed us some waters. She joined me by surprisingly sidling close enough to have our legs touching as we sat side by side. The conversation continued simultaneously with the commencement of the typical progression. Arm around her shoulder, her leg playfully intermingling with mine, her repositioning to have her head lay in my lap with her legs pointing away. Perfect for my hands to do some more exploring. She felt me growing and didn’t mention it, but suggested relocating. Upstairs and water bed. This might sound fun and be nice for a nap, but it was awkward and not as functional for what we were getting up to. Clothes off and you know where my focus is. I’m estimating they’re H cup based on comparative picture research, but never asked. Anyways, they were incredible in all ways. So hefty, and with deliciously large areolas. They sagged, of course, and nipples pointed more down than at me when she stood, but it is perfection to me. Chubby belly that hung down a bit, skinny hips and flat butt that were enjoyable in the contrast they gave to her amazing bust. Her body knew what to highlight and didn’t want to take attention away. Low-trimmed bush between her tight, inflexible hips and legs that I had to loosen up. My eyes have not seen a better sight than her laying on her back. Each splayed out to its respective side and slowly flopping with our and the bed’s waves of motion. She is the least active partner I have had. She never said something to the effect, but maybe it was me. I was fine with her allowing me to do most of the work though. I had plenty of fun with her assets between rounds, but left after the next go. She came to my apartment the next weekend and we fooled around a bit, but she just wasn’t as comfortable. I visited once more around Christmas when her daughter was out of state again, but it fizzled after that. It was fun, but the chemistry wasn’t strong.
The Importer, 57 years old: Short, brown, frizzy hair, brown eyes, 5’1″ (she was adamant I knew she was taller than 5 feet nothing), flawless, olive skin, curvy figure. I typically travel for work 3 or 4 times a year, and one of these was coming up a couple weeks after the start of the New Year. I had the idea to create a new profile in the major city I was visiting and sent out feelers to see if any women would want to get acquainted online before meeting up while I was in town. Most women thought I was looking to cheat or they didn’t want something destined to be so brief. She thought I was pulling her leg and that there was no way a guy my age could find her physically desirable. I thought she was joking because I know I’m not alone in my tastes, but she insisted younger guys never messaged her. She was interested, but still thought I was playing some cruel joke on her. I did my best to convince her of my desires. She was convinced. I was only in town for 3 nights and she had a conflict the first night. We agreed on meeting the second night at a bar down the street from my hotel once dinner with my client had finished up. It was after 9 before I was free, but she was still game. Her personality on first impression was so perky and bubbly and more befitting of a 20 year old college girl that is slightly tipsy at a party. And maybe she was trying to relive something. A cocktail each and we were more than ready to find somewhere more private. We made it to my room and stood there for a second looking at each other. She was still waiting for me to say April Fools, but that wasn’t coming. We embraced, hands searching, mouths meeting. Then she led me to the chair in the back corner of the room, sat me down, and started to undress me. She had discussed wanting to do this, and now she was. I was now wearing nothing but a smile. I managed to get her top and bra off during this. She has D cup breasts (told me) that sag but maintain a perkiness about themselves by pointing straight ahead, dark red areolas, and the best (just perfectly soft and plump in a great way) tummy I’ve seen in person. I would find out later that she was completely bare below besides a very shortly trimmed triangle pointing in the right direction. Her hands and mouth took great care of me. I think she might have enjoyed it more I did. She is the first woman I’ve been with of any age that was solely focused on my needs, and I actually believe she would have been fine with that being it. I insisted on returning all favors though. And did. We got another round in after my exploration. She was self-conscious about her flat butt. I thought it was cute, and it looked great up in the air and framed by her wide hips. I left some of me on her sexy tummy. By then it was past midnight and I walked her to her car. She came back for another round the next night and the next day I headed home. There have been obvious reasons for me not going on another business trip since, but if I ever do then I just might have to try for a sequel. She sent me an email update a month later. She had been converted. She started going on the prowl by initiating conversations and had seen a 34 and 25 year old since our time together. I had a new woman to tell her about too.
The Redhead, 54 years old: Fairly straight, red hair halfway down her back, freckles everywhere except for between her legs(I would find out why), blue eyes, 5’6″ (estimated). She has a bohemian style of dressing to go with a similar personality. Toned and more slender build from yoga. She doesn’t have tons of curves, but redheads are my weakness. After dipping my toes into a new pond with the city I had just visited, I decided to widen my own pond by increasing my distance search radius. We talked for a couple weeks and then one clear, chilly Saturday morning I asked about her plans for the day. She was off to the hardware store. I responded with some immature line about coming over and helping with any hammering she needs. Sometimes it works and it did that day. I was on my way. The hour drive gave her time to run her errand and my mind plenty of time to race with lustful anticipation. She has a beautifully unique home on a decent chunk of land out in the middle of nowhere. She let me inside and gave me a quick tour. When we got to the kitchen she offered to make drinks. It was past noon at this point so a gin and tonic for each of us. We settled in her living room on separate chairs and talked. We talked for probably an hour. She had been through a lot the previous few years, but was optimistic and graceful in her speech. She is so easy to talk to, and we seamlessly wove from topic to topic, sad to serious to silly to sensual. She is an amazing woman. Our glasses had long been empty when she suggested moving to her bedroom. She insisted on needing a shower and told me to make myself at home. I countered by joining her. We undressed while stealing glances at each other and hopped in. She has B cup breasts with only a slight sag and freckles surrounding her pink nipples. Flat stomach, medium width hips, and a juicy apple bottom butt. Her trimmed matching carpet led to the best pussy I’ve seen on any woman. When I got more acquainted with her later I saw her perfectly pink lips and flawless freckle-free pale skin surrounding it. I’ve never met one I didn’t agree with, but she has just the best compromise of not too little and not too much going on down there (and the pinkness seals the deal). We took turns getting each other sudsy and squeaky clean. By the end of her handiwork she had a place to hang her towel. Onto the bed and after adding protection she was immediately on me. She knows how to ride a man, and when to ask for what she needs and when to take it. So much fun to please. I was worn out after three rounds. It was dark by the time I left that day. We got together three more times over the next month, but then coronavirus happened. We maintained correspondence and she invited me back over in early June when things were looking optimistic. We were both starved for the touch of the opposite sex. Another magical day. Between rounds we went out in the sun on her back deck with nothing on at all and talked some, were quiet some, and stared at nature. And that’s where all of those freckles come from. We’ve continued to stay in touch, but haven’t gotten back together again. She visits her mother often and with this new wave has been understandably extra cautious. I have a feeling we haven’t seen the last of each other though.
Source: reddit.com/r/gonewildstories/comments/htb0mh/celebrating_the_uniqueness_of_mature_women_a_mans