Unexpectedly slept with [m]y long term family [f]riend

Obligatory story from a few years ago, but I figured that you guys would appreciate it. Just to give you all some background context on this. So [m]yself and family [f]riend. Let’s call her Emily, we grew up together from really early teenage years. As we were growing up, I would have considered her her my best friend for a good while.

Her mum used to tease her quite frequently about me being her boyfriend because of how often we used to hang out, and while I’ve always found her really attractive we were two very different people, we just wasn’t eachothers ‘types” so I never thought to even try/ just didn’t cross my mind.

As the years went past we did grow apart after moving to separate towns but still made an effort to keep in contact & meet up for lunches or go shopping that kinda thing, each time we met seemed to get further apart from the last until eventually we had definitely drifted apart as “best friends”

[m] Getting caught by the park security

This is another one of those obligatory “happened a few years ago” but I figured that someone would enjoy this one.

I had not long been out of university at the time, it was the summer holidays so I did what any single graduate on summer break does. Download a dating app.

Swiping through as you do, came across this particular girl. Thought she was incredibly attractive, she was well traveled & studying for her PhD (according to her bio) on the surface she was the kinda girl that I’d be ‘punching’ above my weight, my confidence at the time wasn’t that great but I swiped on her anyway, you can probably see where this is going but to my surprise she had swiped a like on me?

So we get talking over message to begin with, we went out on a few dates over the weeks that followed, fairly typical date(s) of going out to dinner etc, just trying to get to know her.

Unexpectedly slept with a long term family [f]riend.

Obligatory story from a few years ago, but I figured that you guys would appreciate it.

Just for some background context, [m]yself and family [f]riend. Let’s call her Emily, we’ve grown up together since our really early teens. We were best friends at one point for a while. Growing up her mum would always tease her about me being her boyfriend and although I’ve always found her an attractive girl, I was never really her type and I’m not sure she was mine either. We grew apart a little bit after moving to separate towns but still made an effort to keep in contact & meet up for lunches or go shopping that kinda thing, each time we met seemed to get further apart from the last.

Fast forward to 2018, it was mid/late November and we’d met up for lunch to have a catch-up, I hadn’t seen Emily in maybe 6+ months or so, it was super casual nothing that we hadn’t done before. While at lunch Emily mentioned that one of her friends was having a night out for her birthday & asked if I wanted to go? I’m a bit of an introvert, so I hesitated but ultimately agreed to go, I hadn’t had a night out for a while & figured it would be nice to get out for a night.

[m] Getting caught by the park security

This is another one of those obligatory “happened a few years ago” but I figured that someone would enjoy this one.

I had not long been out of university at the time, it was the summer holidays so I did what any single graduate on summer break does. Download a dating app.

Swiping through as you do, came across this particular girl. Thought she was incredibly attractive, she was well traveled & studying for her PhD (according to her bio) on the surface she was the kinda girl that I’d be ‘punching’ above my weight, my confidence at the time wasn’t that great but I swiped on her anyway, you can probably see where this is going but to my surprise she had swiped a like on me?

So we get talking over message to begin with, we went out on a few dates over the weeks that followed, fairly typical date(s) of going out to dinner etc, just trying to get to know her.

Unexpectedly sleeping with a long term family [f]riend.

Obligatory story from a few years ago, but I figured that you guys would appreciate it.

Just for some background context, [m]yself and family [f]riend. Let’s call her Emily, we’ve grown up together since our really early teens. We were best friends at one point for a while. Growing up her mum would always tease her about me being her boyfriend and although I’ve always thought she was a pretty girl, I was never really her type and I’m not sure she was mine either. We grew apart a little bit after moving to separate towns but still made an effort to keep in contact & meet up for lunches or go shopping that kinda thing, each time we met seemed to get further apart from the last.

Fast forward to 2018, it was mid/late November and we’d met up for lunch to have a catch-up, I hadn’t seen Emily in maybe 6+ months or so, it was super casual nothing that we hadn’t done before. While at lunch Emily mentioned that one of her friends was having a night out for her birthday & asked if I wanted to go? I’m a bit of an introvert, so I hesitated but ultimately agreed to go, I hadn’t had a night out for a while & figured it would be nice to get out for a night.

[m] Getting caught by the park security

This is another one of those obligatory “happened a few years ago” but I figured that someone would enjoy this one.

I had not long been out of university at the time, it was the summer holidays so I did what any single graduate on summer break does. Download a dating app.

Swiping through as you do, came across this particular girl. Thought she was incredibly attractive, she was well traveled & studying for her PhD (according to her bio) on the surface she was the kinda girl that I’d be ‘punching’ above my weight, my confidence at the time wasn’t that great but I swiped on her anyway, you can probably see where this is going but to my surprise she had swiped a like on me?

So we get talking over message to begin with, we went out on a few dates over the weeks that followed, fairly typical date(s) of going out to dinner etc, just trying to get to know her.

I [M29] unexpectedly slept with one of my [f]riends, and I’ll never forget it

Obligatory this happened a few years ago, but it’s a story I’ll never forget.

Just for some background context, myself and [f]riend. Let’s call her Emily, she’s a long term family friend & we grew up together in the same town for a while in our early teens but eventually we both moved away with our parents to different places. I would have considered her one of my best friends at one point but as years went by, we drifted apart with me going off to university ect…

Fast forward to 2018, it was late November and we’d met up for lunch to have a catch-up, super casual nothing that we hadn’t done before. While at lunch Emily mentioned that one of her friends was having a night out for her birthday & asked if I wanted to go? Being the introvert that I am, I hesitated but ultimately agreed to go, I figured a night out would do me some good.

I [M29] unexpectedly slept with one of my [f]riends, and I’ll never forget it

Obligatory this happened a few years ago, but still turns me on thinking about it now.

So just for some background context, myself and friend. Let’s call her Emily, we’ve grown-up together from our early teens, then in our later years we moved to different towns with our parents but kept in touch/ visited each other from time to time. We’ve never been anymore than good friends, inevitably as the years went by we’d drifted with me being off at Uni ect…

Fast forward, it was late November & we’d met up for lunch to have a catch-up, while at lunch Emily mentioned that her friend was having a night out for her birthday & asked if I wanted to go? Being the introvert that I am, I hesitated but ultimately agreed to go (why not)

So a few weeks later, I drove up to her mum’s house for the night out (Where she was living at the time) she lives around an hour away so offered to let me sleep on the sofa for the night as I’d certainly not be driving back that night.