Author: Accomplished_Tell

My [M] night with the older family friend [F]

For many years, my family would go to a Christmas party at Melanie’s winter cabin. Melanie lived in our neighborhood and had similar aged kids as my siblings and I, and my mom became very friendly with her as the years passed, so much so that we even attended her annual Christmas party at her winter cabin that was only about 45 minute away from our neighborhood. The parties were always a blast growing up, lots of kids running around and the parents all having a good time.

As the years passed, Melanie separated from her husband, and us kids all went off to college. I stopped attending the annual party once I turned 18. My mother and Melanie’s friendship became strained (I think it was related to fallout from Melanie and her ex-husbands divorce) and my parents also stopped attending the party. Read more »

eating my boss’s pussy [MF]

I [31M] have always admired my boss [48F]. She is extremely intelligent and challenges me with difficult and interesting projects. While I had always found her attractive, our relationship was 100% professional. That being said, I would still innocently check her out. I’m not one who is overly fond of legs in particular, but my boss has amazing legs that are always standing out in her designer shoes and business attire. Like I said, our relationship was always professional, but of course my mind would wander from time to time as she is attractive and also the power dynamic is a bit of a turn-on. I should also mention that I am fairly certain she caught me admiring her legs from time to time, but it was never brought up, and I was always careful to never overstep or be too obvious.

We had a big presentation we were preparing for and worked extremely hard as usual to set ourselves up for success. We traveled out of city to make this presentation, as we often did. It was a hot August day and she was dressed in a gorgeous but also professional summery dress. She was very tan at this time of year and as usual, her legs looked amazing as she strutted down the city streets in heels. I noticed all the looks she was getting as we passed by people on the streets. She always looked good, but on this day she reallllly looked good. Read more »

Blown by the GILF next door PART II [MF]

The following morning I texted Erica because I didn’t want it to be awkward between us and I was also very turned on thinking about what happened the previous night. It was a few hours before she responded. She assured me nothing would be awkward on her end but she didn’t take my bait when I tried to get a little “naughty talk” started.

I saw her outside a couple times the next week and it was fine – we made our usual small talk, but nothing more than that. It was now Friday and I was starting to think of weekend plans. I ended up getting a text from someone else, my off and on fuck buddy, Jill. Jill was 22 and she had a tight little body with a bubble butt, tan and dark haired. Jill had a high sex drive and we had a purely sexual relationship. Jill ended up coming over that night.

We fucked twice and she left. It was hot as usual, but I had found myself thinking of Erica as I was finishing fucking Jill for the second time. It didn’t make sense to me as a thought about it – why was I thinking of my 60 plus year old neighbor Erica while I was with Jill, an extremely sexy young woman who was very fun to fool around with? Read more »

Blown by the GILF next door after telling her about my girl troubles [MF]

I [25M] had just gotten home from a night out with some colleagues, which included me getting shutdown when I told a coworker I had feelings for her. I was feeling down as I got out of my Uber and was heading into my apartment. My neighbor, Erica, was outside having a smoke. As usual, I stopped to make some conversation with her.

Erica was in her 60s. She was a great neighbor and had a good sense of humor and way about her. I didn’t know her too well, but we would always make small talk as we’d see each other often.

Erica was pretty for an older woman and kept herself in decent shape, but I’d never considered anything in terms of being sexually attracted to her. I was mostly focused on girls my age, particularly the girl from work who had just told me she wasn’t interested.

Erica could tell I was upset so she asked what was up. I told her simply “girl problems but I’ll be fine”. She kind of laughed and asked if I wanted to talk about it over a beer. I said yea why not and she led me inside her apartment. Read more »

The BBW redhead in a black velvet dress [MF]

It was a snowy Friday night in January. My friends and I had plans to go out for drinks at a really nice local hotel. It was a popular spot and the place was lively as we entered and approached the bar to order drinks. We found a little spot to stand around and socialize while we were of course examining the potential prospects in the room.

While running my eyes across the room I noticed a redhead woman. I did a double-take after noticing the black dress that was hugging her figure. I couldn’t take my eyes away from how her black dress was hugging against her round ass. She was surrounded by a couple other women and a group of 5 or so mostly older men who all looked very professional.

Our night went on as my friends and I put back drinks and started socializing more with strangers. The redheaded woman was still in her group so I didn’t bother making my way over to her, though I could not stop glancing in her direction every few minutes. Read more »

An unexpected happy ending [MF]

I had recently finished moving into an apartment in a different part of my city. I was tired and sore and decided a massage would be a great way to relax. I googled massage places around me and called one that was in walking distance. A woman answered and said her last slot was open at 6pm.

I hopped in the shower, changed, and made my way over to the massage. This place didn’t have many reviews but I was just happy to get an appointment last minute and would make the best of it. When I arrived I was greeted by an Asian woman, I’d say she was about 45 and very average looking wearing an oversized t shirt and leggings.

She walked me into the room and left while I undressed completely. I noticed the towel that I was to drape myself was small, more like a hand towel. I realized this might be a place that offers “extras”. I wasn’t looking for that type of massage but I trusted I had the self control to pump the breaks if I felt any lines were being crossed. Read more »

The MILF Chronicles: Pam [MF]

We’d been messaging online. I was 25 and she was in her late 40s. She (Pam) was a teacher and a single mother of young kids. We lived close by and I found her pictures to be very attractive and I liked her style. She had a pretty face and could tell she had large breasts even though she was well covered in all her pictures.

She admitted she thought I was handsome and charming but wasn’t sure how she felt about our age gap. I told her I understand where she’s coming from and explained that I was always attracted to older women and had recently had a positive experience that confirmed that strong attraction (see my previous post for that story).

After a month or so she texted me saying she was finally interested to meet in person. We would meet the following day after work – she would pick me up from the train station and drive us a few minutes to a local bar. Read more »

First time with an older woman turned into my first creampie experience [MF]

I was at the gym on a Saturday morning, getting my lift in when I noticed a sexy blonde woman working out on a machine across from me. I would check her out in between sets and thought I noticed her checking me out a bit as well, but it’s always hard to know for sure in a gym setting. She eventually stood up from the machine and I immediately was drawn to her big butt outlined by her black yoga pants.

She was blonde with shoulder length hair and brown eyes. Pretty in a mom next door kind of way. I knew she was significantly older and I had always had a thing for older women. I was feeling extra horny and I was determined to try and get her number, which is not something I ever cared to try in the gym setting.

She was leaving the gym so I followed her to the parking lot and asked her if she’d be interested in meeting me for a drink. She smiled and chuckled and said she was flattered but that she was older than I probably realize. I was 24 at the time and turns out she was 52. I knew she was older but I didn’t care to explain or offend her. I told her “I’m comfortable with it if you are”. Read more »

I hooked up with my Asian neighbor [MF]

There was a huge language barrier between us but I [26M] could tell from our interactions she [41F] was fascinated with my body/build. I am 6’2 and muscular. Very lean and cut. I wear sleeveless shirts around the house and on a couple occasions ran into my Asian neighbor while wearing my sleeveless shirt. We would often try to make small talk but it was hard for both of us to understand each other, so we’d usually just awkwardly smile and get on with our day.

One day I had ran outside to bring my trash out when I ran into her. I was wearing a cutoff t and my arms were looking swollen from my workout earlier that day. I could see her eyes get big while she looked me over and she even smiled and grabbed one of my arms. I was comfortable with the interaction and just kind of laughed it off. As the day went on though I thought about it more and it got my imagination running. Read more »

My friends mom and the winter cabin – Part 5 and FINAL [MF]

It was now my turn to play out my fantasy. She was very happy with how hers turned out and really wanted to please me in return. I felt a bit silly but my idea was fairly simple – I just wanted to be seduced by an older woman. My idea was that she hired me to to some work on her cabin and I would be outside in the cold working away, and she would be tasked with trying to seduce her young and sexy help inside. I asked that she wear something elegant – playing the role of rich and under appreciated housewife. She ran upstairs to pick something out from her closet while I headed outside to start my work.

I began working on some odds and ends – moving some firewood closer to be brought in, doing some extra shoveling on the back walkways, etc. It was freezing cold, I could see my breath as I exhaled into the nighttime winter sky when I suddenly saw the outside lights turn on. I looked up to the door as I heard it open. She stepped out onto the porch and flagged me over. I approached the steps to see her wearing a dark brown mink coat. It was tied at the taste and ran down just above her knees. She also had high-rise black boots and black thigh high stockings on. She commented on how cold it was and asked if I’d like to take a break from my work and come inside to warm up. Read more »