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”

Fast forward some years, it was my final year of university and 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.

A few weeks later, it’s the night of the party and I drive up to her mum’s house, as she lived over an hour away I’d not be driving back she’d offered to let me sleep on the sofa that night. So I get to her house, drop my things off in the living room for later. We chat/ chill for a few hours until her [f]riend arrives, her [f]riend arrives a little while later & they head upstairs to get ready ect.. we head out for the evening.

We met up with a few others from Emily’s friend group, start at their local pub for a few drinks then move onto some other bars & clubs from there. We get to the end of the night, it’s around midnight at this point we walk everyone in the group home leaving just myself & Emily stumbling back to hers as the last people from the group. It’s the middle of December so it’s absolutely freezing outside.

Emily unlocks the door, we get into the entrance hallway of her house, and just as I turn to go into the living room to head off to bed she turns and says “Hey, don’t worry about staying down here, you can come sleep upstairs with me I forgot to sort the bedding out before we left” so I turned and said “Okay, no worries I’ll grab my things” so I walk into the room grab my things and then follow Emily upstairs. We get to the top of the stairs and she said “I’m just going into the bathroom, I’ll be there in a bit” so I turned left and headed to the bedroom and placed my things down to get myself sorted.

A few minutes later just as I stood getting undressed into my boxers ready for bed, Emily then walks back into the room & goes over to her wardrobe and gets a bed shirt out, then just as I glanced up at her she had unzipped the back of her dress and dropped it to the floor. Now I’ve always found Emily an attractive girl, but that moment my jaw hit the floor.

Believe it or not but in all years I’ve known Emily, I’d never even seen her in a bikini or swimsuit, and yet here she was standing in front of me in a black lace bra & thong my mind had never wandered so quickly! Even with her clothes on, I’ve always noticed she had an incredibly ‘womanly’ figure, very curvy but in all the right places, at that moment I took as many mental photos as I could for the ‘wank bank’ but kept my composure.

However it didn’t last long as before I knew it, she then unhooked her bra strap, then pulled her bra off and let the “girls” out and wow did they drop out, I definitely felt my dick twitch, they jiggled with every movement she made as she then covered them back up with her bed shirt, although I could tell she was definitely still feeling cold from the walk back to the house if you know what I mean.

I tried to be mature about it, just pretend to ignore it so I get into one side of the bed, she follows shortly after and then we switch lights out and I turn over facing away from Emily & close my eyes to try to fall asleep. A few minutes later I hear Emily rustling and then she whispers over to me ‘Hey, can we spoon for a bit it’s still freezing’ so I turn back over like ‘Yeah, sure’ so I turn over and assume the position of the ‘big spoon’ she then nestles herself in against me, I then place my arms around her.

We get comfy & cuddled up, put my arm over her and around her stomach and I close my eyes again to try to sleep however having just seen Emily get half naked in front of me, possibly because of the alcohol as well but I could feel myself started to get really turned on, I could feel my dick getting harder & harder by the minute and despite my best efforts to try hide it at first, but to no avail I was honestly about as hard as I could have been & there was no way she didn’t feel it rubbing/ poking against her ass. She didn’t seem to mind/ say anything so I just ignored it.

We carry on spooning, I’m still really hard at this point but to this day I’m still not sure if I was imagining this due to being drunk or she was doing it on purpose or if she was just fidgeting but it definitely felt like she was rubbing/ grinding her ass against me ever so slightly.

My mind was racing at this point, having known Emily for so many years and having never been this naked/ close to each other before it was a bit weird at first and while I’ve always found her attractive, I never thought anymore of it but the more I thought about it and yet given the circumstances & quite frankly how turned on she has made me feel that perhaps this was it? So as we continued spooning, figured I’d ‘test the waters’ with my arm still over her I decided to start lightly touching around her stomach area with the tips of my fingers. Then gradually moved my hand down towards and then over her navel and then down to the band of her underwear.

Lightly touching just above the band of her underwear, kept my fingers there for a while before I slowly slipped just the tips of my fingers inside the band of her underwear fully expecting her to stop me there but nothing? So I kept my fingers just inside the band of her underwear just for a little bit longer to make sure she seemed okay with it, she gave no indication she wasn’t? Hesitantly I moved my hand further into her underwear and just as my finger tips touched the top of her pussy I could feel a wetness in her underwear so I slide my fingers down over her clitoris & started slowly rubbing/ touching around her pussy. After playing with her for a little bit I could feel her getting wetter so I moved my hand slightly further down and just as I slipped two of my fingers inside her, she let out a little whimper. She felt so wet and so warm it was like finger heaven.

After a few minutes of finger fucking her, Emily grabs my hand and pulls it out from her underwear then turns to face me and pulls herself closer and we start making out, as we’re making out I can feel her fidgeting as I look down she’d pulled her thong off then as her hands come back up she reaches into my boxers with both hands using one hand to firmly hold & start stroking me, it felt amazing in her hand and the other hand to slide my boxers down she pulls my dick towards her then starts rubbing the tip of my dick against herself, still firmly holding my dick she guides my dick towards her pussy, as I bite her lip I thrust my dick all the way inside her letting out a little moan as I enter her.

Still in complete disbelief, all I can remember was how amazing her pussy felt. We continue making out, thrusting into each other harder & faster. I really wanted to see/ make her cum, so I pulled out then rolled her underneath me, placing her legs over each of my shoulders then as I slowly moved my hips back towards her, without any guidance my dick slipped straight back inside her.

Started slowly thrusting in & out with every inch, we continued like this for good while, slowly getting faster & harder. I could feel her start to tense up & fidget around as she edged towards cumming so I take my hand and begin rubbing her clit & she starts to moan a little & starts grabbing the bed sheets, then after a little more time she arch’s her back, all I remember feeling is a rush of wetness filling her pussy as she came, that feeling pushed me over the edge, I kept thrusting for as long as I could but I could feel myself cumming inside her and as much as I’d have loved to have shot ever last drop of cum inside her, we didn’t have anything so I had to pull out as quickly as I could and just as I pulled out shot my load all over the outside of her pussy and over her stomach… It’s not a sight that I’d ever thought I’d have ever seen but damn, she looks good covered in cum!

We both laid next to each other for little while just recovering, before ultimately we passed out after a while at least I know I did, but we woke up the next morning both in a little bit of disbelief of what happened, happened. But she seemed fine with it, and I was definitely fine with it but we agreed that it wasn’t probably the best idea we’ve had together but oh I absolutely don’t regret it in the slightest, one of the best nights I’ve ever had.

Source: reddit.com/r/gonewildstories/comments/xtwdn7/unexpectedly_slept_with_my_long_term_family_friend