Author: Accomplished_Tell

My childhood friends recently divorced mom [MF] part 2

Part one: https://www.reddit.com/r/gonewildstories/comments/12xlf4f/my_childhood_friends_recently_divorced_mother_mf/?utm_source=share&utm_medium=ios_app&utm_name=ioscss&utm_content=2&utm_term=1

The following morning I woke up full of excitement and guilt. I was replaying the events in my head and became incredibly turned on thinking about Sheila. Her soft skin, those big lips, and her natural curvy / slightly chubby figure.

I thought we left things well the previous night. After we fooled around we cuddled and made out for a bit before I made my way home. It was clear that we had both had a fun time together, as unexpected as the night had been.

The more I thought about her the next morning the more turned on I got, and I ended up texting her letting her know how much fun I had and how turned on I was thinking back on our evening.

I waited eagerly for a reply but did not hear back from her until much later that day. She basically agreed it was a really fun night but that’s all it would be. The reasons being our age gap, the whole sons old friend thing, and just her overall stuff going on after her divorce. She wanted to focus on getting into shape physically and mentally. Read more »

My childhood friends recently divorced mother [MF]

I had known her since I was a kid. Her house was one of the spots my friends and I would always be welcomed at. From the middle school years all through high school, we had many good times over at my buddies house.

His mom, Sheila, was a welcoming host, and to be honest I always had a bit of a crush on her. She had dirty blonde hair which she usually kept fairly short but stylish and a pretty face with soft pillowy lips. Something about those lips always lit a fire to my imagination growing up. She also had a curvy, soft body – probably could be considered a little chubby, but to my eyes she always seemed warm and inviting.

I was just a kid and she was happily married, so this was one of those things that I would fantasize about in private moments. As I got older I began seeing her far less frequently but would continue to fantasize about her from time to time.

As the years passed I fell out of touch with her son. I was now in my early 30s and living a few towns over from where I had grown up, and where Sheila still resides. Read more »

I fingered the stranger sitting next to me on the train [MF]

I take the train into the city from my suburb for work. It’s always the same time I take the train, which is about an hour commute each way.

I typically see the same people each day as we are on similar schedules, including this one woman in particular who I noticed kept sitting near me. She is in her late 40s with short curly brown hair. I’d say about average looking at first look, but well-dressed and always appearing put together.

I am in my 30s, tall, fit, with brown hair. I always have a book to read on the train and usually am lost in the book. One day this woman sits next to me in a two seater on a crowded train. She opens up a book and flashes a quick smile that I returned as we make eye contact before both returning to our books.

About 15 minutes later I reached into my pocket to grab my phone. Along the way my hand brushed up against her smooth exposed thigh. I mumbled a quick apology to her for the innocent brush up. She smiled and said no worries. Read more »

A Sensual Evening with my Ex’s Aunt [M] [F]

On a cold December afternoon I received a text from my ex-girlfriend’s Aunt, Paula. Paula was reaching out to see if I was interested in her husband’s golf clubs. Her husband had passed away a couple years prior, when I was still dating their niece, Taylor, and she was finally getting around to going through his belongings. I had a good relationship with her Aunt and Uncle while I was dating Taylor and we always had a fun time together at their family gatherings. They loved to drink and listen to music and her Uncle and I were both big into golf.

I was surprised to receive this text from Paula, but it felt nice that she thought of me when looking to give away the nice golf clubs. I happily accepted her offer and we set up a time for me to stop by her house to pick up the clubs. She told me I could come over Saturday evening. She had a Christmas party to go to but was going to be home until around 7pm. I headed over around 5pm and didn’t want to show up empty-handed, so I stopped to grab a bottle of wine. Read more »

The Surprise Squirter [M] [F]

After weeks of texting, Jane was finally on her way over to my apartment. We had met on tinder anbegan texting frequently. She was 48 and recently divorced with a couple kids. I was 25 and single and looking for a good time. We had both been out drinking when she texted me asking if she could come over.

I left the bar I had been at with my friends and ran home to freshen up. About an hour later Jane arrived. It was clear she was feeling pretty good as well, as she had also been out with friends. After a quick in person introduction and tour we quickly headed to my bedroom.

Jane is very tall for a woman, and must have been close to 6 feet with the boots she was wearing. She was wearing a corduroy skirt that accentuated her long legs and thick thighs and black leather boots that came up high. She had long brown hair and a thick ass. Read more »

My friend wouldn’t eat his girlfriends [F] ass, so I did [M]

I had invited my friend and his girlfriend to accompany my girlfriend and I for a weekend of skiing and drinking at my family’s timeshare. The 4 of us had become close over the years as we approached the age of 30 and were looking forward to a weekend away.

We all got up to the timeshare late Friday evening and we all got very drunk. Late in the night the topic of eating ass came up. We were laughing about how it seemed to be a new “phenomenon”. I proclaimed that I was into it before it became a thing, which made my girlfriend role her eyes at me, “i don’t know, it’s so weird to me, I know you enjoy doing it but it’s just not my thing”.

My friends girlfriend shared that she’d never experienced it but admitted she was curious , “he refuses to try it”, she said as she looked at my buddy. We all joked about it and moved on, and went to bed shortly after. Read more »

The visiting IT trainer [F] invited me [M] back to her hotel room

I had just gotten my first real job in the city and was excited with all that came with it, after having done mostly labor jobs until that point. I had my little cubicle and was finding my way fairly well. I had to go through various trainings as part of the onboarding process, and part of that was an IT training to go over our systems.

The company I worked for has offices in various locations, and the IT training was scheduled to be done remotely, as the woman who was to train me, Karen, worked in an office a few states over. Karen called me and remotely took control of my computer as the training started. We didn’t see each other, so it wasn’t a flirting type back and forth we had, but she was friendly and funny and made a decent time out of what was a boring training session. Read more »

My Internship [M] romance with an older woman [F]

As usual, I waited until the last minute to find an internship that I was required to complete in order to graduate from college. By the time I got around to applying there were hardly any options left. I lucked out and was able to intern at a local recreation center for middle school kids. It didn’t really fit with my studies, but I was desperate, and the Rec center was desperate to get some cheap help.

Two days a week I was to work at the rec center where about 12-15 local middle schoolers would hang out after school. It was a great experience as I got along well with the director of the center and I enjoyed working with the kids. The center had video games, a pool table, and those sorts of activities for the kids to play with. Generally speaking, most of the kids were a bit rough around the edges, often coming from broken homes. Read more »

The mansion meet-up [MF]

“Are you ok with this?” She asked me as she entered into her living room. This was the first time we had seen each other in person. We met on an online dating site that was aimed at younger men meeting older women. The dating app was full of “bots” and fakes for the most part, but I happened to start messaging with a woman, we’ll call her Tracy, who lived a couple towns over from me.

We eventually exchanged phone numbers after messaging on the dating site for a while. Our conversations evolved from getting to know each other, to sharing more pictures, and eventually came more steamy.
We agreed we both wanted to meet up soon. She was in her 40s and appeared to be very successful while I was a senior in college, home on winter break. We were both just looking to have some fun. Read more »

Seduced by an older woman at an an all inclusive resort [MF]

A few years back I took a vacation to a resort with my girlfriend and another couple. It was your average cheapish all inclusive resort. I was in peak shape as I had worked out extra hard knowing we’d be taking this vacation. I was proud to show off my hard work at the various resort pools and beach and I admittedly enjoyed seeing women take notice.

I was 25 and noticed many of the people there were older. Lots of families with kids. There was still some decent eye candy to look at, and the adult only pool ultimately became my favorite spot while on the trip.

On day 2 of the trip I posted up at the pool bar with my girlfriend. An older woman with short brown/reddish was sitting to my left. Her name was Diane. After a couple drinks and small talk, Diane commented on how much my girlfriend looked like her daughter. It was kind of weird but I laughed and said “oh then she must be a beautiful young woman”. Read more »