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.

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’m getting undressed into my boxers read for bed, Emily walks back into the room & goes over to her wardrobe and gets a bed shirt out, then just as I glanced up she’d taken off her dress and my jaw hit the floor. Underneath her dress, she had been wearing this matching black lace bra & thong, now I’ve always noticed she had a good sized ass but I’d never seen it with such little fabric covering it but her ass looked good! And before I knew it, she’d unhooked her bra & taken it off to let the “girls” out, and wow did they drop out! My eyes lit up for a brief moment before she covered them back up with a bed shirt but I absolutely felt my dick twitch.

Up until this point in all the years I’ve known Emily, I’ve never even seen her in a bikini or even a swimsuit for that matter & she felt comfortable enough to just strip off half naked in front of me, but damn I wasn’t complaining that mental image was honestly ‘Wank bank’ material forever.

Still very much processing all this, try to be mature about so we get in bed, switch lights out and I turn over to head of to sleep room very much still spinning… Little while later, Emily whispers over to me ‘Hey, can we spoon for a bit it’s freezing’ so I turn back over like ‘Yeah, sure’ so I turn over and assume the position of big spoon, she then nestles herself in against me. Friend’s do this sorta thing right? I was trying to be cool about it but that mental image of her undressing in front of me was making it, cough* hard.

As we were spooning I could feel my dick getting harder by the minute, there was no way she couldn’t feel it rubbing against her incredibly soft ass. After maybe 5/10 minutes I was about as hard as I could be at this point… I tried to be mature & ignore it, w/e but as we’re spooning and to this day I’m still not sure if I was imagining it 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 her ass against me.

As mentioned before I’ve known Emily for a long time & we’d never been this ‘close’ before, I’ve always found her really attractive growing up but it had never gone any further than that but given the circumstances, I was so turned on at this point that if anything were to happen then perhaps this was it? As we continued to spoon I was lightly touching around her stomach area. Then gradually moved my hand down towards and then over her navel and then down to the band of her underwear.

Slowly I slipped just the tips of my fingers inside the band of her underwear fully expecting her to stop me there but nothing. 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? Hesitantly I moved my hand further into her underwear 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 w/e

Source: reddit.com/r/gonewildstories/comments/wtvynl/unexpectedly_sleeping_with_a_long_term_family