Author: Spirited-trouble

Twice my age, Two times as fun! [hotel sex], [morning sex], [heels], [mature], [MF]

*I am reposting this story- I shared it a few months ago, but removed it for some personal reasons.*

This is the second and final part of a true story from about a decade ago- for me, a memorable and sex life-changing experience. You can read about our [first encounter here.](https://www.reddit.com/r/gonewildstories/comments/hqecwi/amazing_encounter_with_a_woman_twice_my_age_milf/).

Disclaimers: Names changed for fairly obvious reasons. Additionally, if uninterested in the buildup, readers can skip to the **first and second parts with sex below, as this is a fairly long story.**.

The ‘Cast‘: Me: ‘D’ Six feet tall, 26 years old at the time, athletic white guy. Her: ‘Kari’ about 50+ years old, white, petite and athletic/muscular, sandy blonde hair and about 5’5’ (with A/B-cup breasts).

*****

The morning I left Kari’s house, she told me she’d keep my number. I wasn’t realistically expecting to hear from her again. At twice my age, we were at such different places in life and I had no expectations of any sort of relationship with her. To quickly recap: I was heavily invested in my new job and she was on the backside of a divorce and teenagers. Read more »

Intimate Sex during a One-Night Stand [sensual], [oral], [cheating], [MF]

This story is about a one-night stand which started online. Be forewarned, it involves infidelity, so if you aren’t interested, stop reading now.

Me: “D,” White, mid-thirties, average/athletic build, about six feet tall.
Her: “J.” White, Mid-thirties, green-eyed redhead, average/slim build with small breasts.

****

During a weeklong business trip, I’d casually reached out online to a handful of women in the city I was staying to see if there was any interest. Nothing really worked out and my half-hearted efforts fizzled after the first two days.

The night before I was going to fly home, I was surprised to see my inbox had a private message. She happened to be online and we messaged back and forth.

Basically, a married woman (I’ll call her ‘J’, based on her screen name and refusal to share our names) my age was also passing through the city for work and obviously was looking for someone. She didn’t care that I was leaving in a few hours. We swapped photos- she was an attractive and slim redhead, with green eyes, wearing gym clothes in both pics she’d sent. Read more »

Amazing Encounter with a Woman Twice my Age [milf], [kinky], [MF]

*I am reposting this story- I shared it a few months ago, but quickly removed it for personal reasons.*

This is a true story from about a decade ago- for me, a memorable and sex life-changing experience. I’d never been with a older woman before (or since, I suppose) who’d been quite as sexually confident and assertive.

Disclaimers: Names changed for fairly obvious reasons. Additionally, readers can **skip to the marked foreplay and sex parts** below, as this is a fairly long story.

The ‘Cast‘:
Me: ‘D’ Six feet tall, 26 years old at the time, athletic white guy.
Her: ‘Kari’ about 50+ years old, white, petite and athletic/muscular, sandy blonde hair and about 5’5’ (with A/B-cup breasts).

*****

It started at a local bar. I’d just ended a long week of work and was simply intending to eat dinner and head home for some needed rest. As I was finishing my last beer for the night, an older woman and her friend sat down beside me at the crowded restaurant.

I did an awkward and probably very obvious attempt to pretend like I wasn’t checking her out. She had a wonderful sundress and heels and I quickly noticed her sleek shoulders and toned, tanned legs. Read more »

Jae keeps her “client” wanting more- Escort Role Playing! [MF]

This story is for a reader who reached out to me with a suggestion recently.

It was a rainy Saturday night. I’d been talking to a woman throughout the week who wanted to meet up for a drink (and more, for a price, she’d implied) at a local hotel. After getting my room key, I quickly found her, sitting at the middle of the hotel bar.

She wasn’t hard to miss. She was already flirting with the bartender, who was eager to be talking to her. In her mid-thirties and with long black hair, she was dressed in tight jeans, black stiletto heels and a flowing, sparkly top, complete with a lot of makeup and big jewelry. She was definitely curvy, which I didn’t mind at all, but still athletic and her hips were highlighted by her tight jeans. I felt a pang I’d jealousy and excitement, as the bartender was clearly into her, too.

I walked right up to her and said “Hi, Jae.” Her eyes lit up and she gave me a kiss on the cheek. She wore bright red lipstick and some dark eyeliner that drew out her big brown eyes. “Hey guy, are you going to buy me a drink or what?” Read more »

Downtown Hotel Room Window [MF]

Last fall, Jae attended a conference for her work. The conference, complete with “My Name Is:” type stickers worn and TV screens displaying which lectures were assigned to each Ballroom, was held in a convention center and hotel near our city.

We couldn’t have been less interested in the conference itself. But her event concluded with a banquet on last night.

It was a promising opportunity to drink on the company’s tab and take a getaway, so we’d decided to attend the banquet and rent a hotel room. The room was on the second floor and its huge floor-to-ceiling windows overlooked a crowded city street, shops, bars and courtyard below. After we checked in, we spent some time people watching the tourists below.

Hours into the banquet, we returned to the room. We’d gotten bored (and horny) after forced social time with people from work. Jae claimed to a group of colleagues she wanted to get new shoes from the room- that her heels were too painful.

Back in the room, we instead drank and laughed and eventually took pictures in the room; it started as silly, the became something else. Jae’s red dress complimented her dark skin and curvy figure nicely- absolutely irresistible. Read more »

Not a Threesome, but quite a show! (Long) [MFF]

Me: ‘D,’ mid-30s, average/athletic white guy, about six feet tall.
Her: ‘Jae,’ mid-30s, mixed Asian-Pacific, about 5’7”, long black hair, curvy build, with wide hips (with small B/C-cup breasts)
Her Friend: ‘Sara,’ mid-30s, white, about 5’9”, average build, short brunette hair (with large natural DD/E breasts).

Disclaimer: Names changed from real people. All of the conversations and texts are from the best of my recall. Because this story is long, I’ve marked the part with sex.

Last summer, Jae’s close friend from college visited to spend a week at our place. Jae had had introduced me to Sara years ago, when she was going through a divorce. Maybe I thought more about it than I should’ve, but back then, Jae often teased about wanting me to sleep with Sara.

A few days into her stay, I met Jae and Sara at a mutual friends’ pool for drinks.
Jae wore a black one-piece, with her hair down low. Jae’s suit left only a little to the imagination, her wide ass and hips visible. (I knew that underneath Jae preferred to kept herself hairless.) Sara on the other hand wore a high waisted two-piece. Her top covered, but pushed together her massive breasts and gave a hint of cleavage. Read more »

MILF Morning Sex (“Rocks my World“ Conclusion) [MF] [No Regrets]

This is the finale to a trio of encounters I had with an amazing older woman a few years ago.

Link to Part One is located here: /r/gonewildstories/comments/eucgx5/milf_twice_my_age_rocked_my_world_mf/?utm_source=share&utm_medium=web2x

Link to Part Two is located here: /r/gonewildstories/comments/f0yh1z/milf_rocks_my_world_again_mf/?utm_source=share&utm_medium=web2x

Disclaimer: Names have been changed for obvious reasons. Actual conversations and texts are from the best of my recall.

The cast:
Me: ‘D’ 26YO at the time, athletic white guy, about six feet tall.
Her: ‘Kari’ about 50YO, white, petite and athletic/muscular, sandy blonde hair and about 5’5’ (with A/B-cup breasts).

A shrill and unfamiliar alarm opened the peaceful silence. I lifted my head and awoke to a hotel room from the night prior- foggy from the shots of rum chased with beers. I watched Kari stride, fully nude, to the curtains and open them, letting in the soft blue light.

5:45 AM displayed on the clock. Despite the fit, naked woman sharing the room, I buried my head in the pillows in protest. “Uggh, no way,” was all I could manage.

Kari laughed huskily and slid back into the bed aside me. I felt the sheet slowly lift from my body, then her fingertips trace along my shoulders. I shivered as she slowly traced along my spine, lower and lower. Read more »

MILF rocks my world again! [MF]

This is a continuation of a story from a few years ago. After recently posting the story of my (first) amazing hookup with an older woman, I feel like I had to post what happened next.

Link to Part One is located here: [https://www.reddit.com/r/gonewildstories/comments/eucgx5/milf_twice_my_age_rocked_my_world_mf/?utm_source=share&utm_medium=web2x](https://www.reddit.com/r/gonewildstories/comments/eucgx5/milf_twice_my_age_rocked_my_world_mf/?utm_source=share&utm_medium=web2x)

Disclaimers: Names have been changed for obvious reasons. Actual conversations and texts are from the best of my recall.

Since this is a long story, readers can skip ahead to **The Part with Sex** if uninterested in the background and buildup. However, I promise I’ve attempted to write it to make it worth the whole read.

The cast:

Me: ‘D’ 26YO at the time, athletic white guy, about six feet tall.

Her: ‘Kari’ about 50YO, white, petite and athletic/muscular, sandy blonde hair and about 5’5’ (with A/B-cup breasts).

The morning I left Kari’s house, she told me she’d keep my number. I wasn’t realistically expecting to hear from her again, as our respective lives could not have been more drastically different. Read more »

MILF twice my age rocked my world! [MF]

This is a true story from a few years ago. I’ve thought back recently to what I would consider a memorable and sex life-changing experience. I’d never been with a older woman before (or since, I suppose) who’d been as sexually confident and assertive. I’ve felt encouraged by a lot of Redditors sharing great content, so I chose to share one of my own experiences.

Disclaimers: Names changed for obvious reasons. Additionally, readers can skip to the marked foreplay and sex parts below, as this is a fairly long story.

Your cast: Me: ‘D’ 26YO at the time, athletic white guy, about six feet tall. Her: ‘Kari’ about 50YO, white, petite and athletic/muscular, sandy blonde hair and about 5’5’ (with A/B-cup breasts).

It started at a local bar. I’d just gotten off a long week of work and was simply intending to eat dinner and head home for some needed rest. As I was finishing my beer for the night, an older woman and her friend sat down beside me.

I did an awkward and probably very obvious attempt to pretend like I wasn’t checking her out. She had a wonderful sundress and heels and I was really drawn to her sleek shoulders and toned, tanned legs. Read more »