Obligatory 'this is an old story but I wanted to share it anyway' Just for some background, my best (f)riend who we'll call 'Emily' we grew up together in the same town from the age of about 10. Our respective grandparents were friends ect.. Anyway, very average friendship for a lot of our teenage years going out shopping and whatever together. Her mum would tease us constantly about being a couple ect. and while I did think she was very pretty. We were very different people personality wise, I was a lot more introverted back then to what I am nowadays where she was very extroverted.
By around our mid to late teens, we'd both moved away to different areas with our parents, but we both made efforts to catch up/ go shopping, talk to each other about our relationships ect. we was about as close as friends as the opposite sex could be at least imo. However as the years went by we'd drifted apart, I'd gone away to university and she was working here & there.. but still kept in contact from time to time just not as much as we once did.
Fast forward, it's mid November and we'd arranged to meet up for lunch, nothing that we hadn't done 100 times before. As we're chatting she mentioned that she'd not long broken up with her then ex-boyfriend (nobody in her family liked him) I was glad for her, she seemed way happier now (he was a PoS from what I'd heard from her family) We get to the end of lunch and she had to dash for an appointment or something, but just before we parted ways she turns to me and says 'oh, btw my friend is doing a bar crawl in a few weeks for her 21st birthday, do you want to come out with us + few of our friends?'
Being the introvert I am, I hesitated for a moment as I didn't know any of her friends but ultimately decided 'why not' I'll be drunk anyway... A few weeks later it's the night of the bar crawl & I drive up to her house around mid-day. She lives about an hour away, so she said I was welcome to sleep on the sofa for the night as I wouldn't be able to drive back home for obvious reasons.
I arrived at her house, I placed my overnight bag in the living room for later and we chill/ chat for a few hours until her [f]riend arrived, at what point they both disappeared upstairs to go get ready ect.. so I sat downstairs, scrolling on my phone usual stuff for a bit then got changed downstairs.
A while later they both appear from upstairs, both wearing fairly long tight fit dresses, Emily has a very curvy hourglass like figure so it hugged her curves really well and she certainly caught my eye for a moment. Anyway the three of us head out for the evening & meet up with the rest of her friend group, we then head off to a number of bars & pubs and by the end of the night it's around midnight and I'm about as drunk as I possibly could be.
We gather everyone from the group up and start walking everyone home, dropping off each person as we go until it's just me & Emily left stumbling back to her mum's house at 1AM in the morning in the middle of December so it's absolutely ice cold outside, luckily I had my beer jacket on so I didn't feel it that badly but I could see Emily was shivering so I tried huddling up to see if that would help.. it didn't.
Anyway, we rush up to the front door and we get inside. I turn and head to the living room while Emily locks the door behind us, then just as I turn to say 'goodnight' ect.. to go to bed, Emily then looks at me and says 'oh! I forgot to get the extra bedding out, do you want to just sleep upstairs with me?' Being quite drunk at this point all I wanted was to go to bed and sleep so I shrugged and said "Yeah, okay" so I turned and grabbed my overnight bag and followed Emily upstairs.
We get to the top of the stairs, Emily then turns and points to her bedroom door and says "my room is the one at the end, I'll be there in a bit" she then heads into the bathroom and I stumble my way across the hall to her room. I set my things down on the far side of the room and very quickly get undressed leaving just my boxer shorts on and get under the covers.
Short while later, I hear Emily walk into the room so I looked up to see how she was doing thinking she'd been and thrown up But as I looked up & before I could say anything she headed over to her wardrobe, unzips the back of her dress dropping it to the floor, revealing a matching black bra & thong. She then opens her wardrobe, grabs a t-shirt with one hand and then with the other unclasps her bra and drops it to the floor, leaving her very busty chest exposed long enough that I caught a glimpse of her boobs and I was not disappointed. In all the years I've known her, I'd never even seen her in a bikini let alone nearly fully naked so I was a little lost for words.
Anyway, she quickly then slips her bed t-shirt on then turns towards the door and switches the light off & then gets into the other side of the bed and say goodnight to each other. As I laid there it wasn't just the room that was spinning.. the mental image of Emily half naked in my head this was getting harder (quite literally) could feel my was cock semi hard at this point.
I tried to try ignore it and just go to sleep, however a little while later, Emily then turns to me and says "Do you mind if we spoon for little bit I'm still freezing cold" me thinking nothing if it, I respond back with "Yeah, sure" so I turn over into position and tactically tuck my cock between my legs, Emily then flips over and placing my arms around her she nestles herself into me, I remember her ass cheeks feeling very cold against my thighs.
Some time goes by and I'm still trying to fall asleep at this point, however I could feel Emily fidgeting or something against me and to this day I'm not sure if it was ever intentional but whatever she was doing, it was causing her ass to grind/ rub up against me and with her only wearing a thong and me in boxers it wasn't long before I could feel myself getting turned on from the motions, and my tactical tuck didn't last long, my cock getting harder and hard until it was fully nestled between her ass cheeks like a hotdog between two very soft buns
I was certain she would say something there was no way she couldn't feel how hard I was but after like 10 minutes of laying there she never said a word. I was so turned on at this point and also so unsure what to do, She could definitely feel me pressed against her but didn't say anything, was this a sign? I went back & fourth in my head for a good while before deciding to 'test the waters' so with my arm around her, I lifted her top slightly and just started to lightly tickle/ rub part of her tummy and with her giving no reaction, in my head I start to think 'Okay, no reaction she's not interested so I should just stop' so I did but to my surprise she then whispered 'You can carry on, that felt nice'
So with that I carried on lightly tickling her stomach and around her hips for a while, It felt incredibly intimate my head kept whirling with thoughts 'Is she into this, does she want something to happen?' so to stop all these crazy thoughts I decided to take another step thinking she would put a stop to it and end these ideas in my head so I gradually started moving my fingers further down her stomach just above the band of her underwear, again light tickles but no reaction? Okay let's take it a step further and slipped my fingertips just inside the band of her thong to see if she'd react but nothing?
At this point I'm thinking to myself 'Okay there is no way this is going any further, this is crazy?' my heart was racing but my fingertips at this point were inches away from her pussy so I decided to just go for it and slipped my fingertips between her lips and started rubbing. I could hear her exhaling every few minutes..
A little while later I see and feel her hand reach backwards, she starts to rub my cock through my boxers for a brief moment before slipping her hand inside the band of my boxers and very quickly grabbing the shaft of my cock and starts stroking me. We must have been touching each other for like 10 minutes before I then felt Emily's hand fumbling around grabbing at the waistband of my boxers to pull them down my thighs.
Pulling my hands away from Emily to take my boxers off the rest of the way, I see Emily in the corner of my eye grab her thong and pull it down and kick it off onto the edge of the bed then, she reaches back behind grabs my hip and pulls me back in only this time as I start getting close I feel her grab my cock and start to rub it against her pussy, teasing herself with the tip of my cock before she then guided it inside sliding all the way inside before starting to slowly thrust..
Still in complete disbelief, she felt incredible the feeling of her ass bouncing against me as she thrust herself back, we cuddle fucked for a good 10 minutes and which point I decided to whisper into her ear "lay on your back" so I pull out and Emily turns to lay on her back. Then getting on top of her, I proceeded to grab her legs and lift them up over each of my shoulders, then with my cock teasing & rubbing it against her pussy lips before slipping it back inside.
Holding her legs back, I started thrusting into her slowly and deeply to begin with, both heavy breathing and letting out sighs between thrusts. I could see her boobs jiggling through her PJ top, her nipples slightly erect and poking through. I then lean and push into her, biting her bottom lip and starter thrusting harder. It felt so intense and so sensitive, I could feel myself edging closer but I didn't want it to finish so fast so I pulled out and immediately moved my face from hers down to her pussy and started to eat her out for a while, few minutes past I feel Emily's hands grab my head and lightly tug to pull me back up so I kiss my way back up her body and as my face reaches hers, my cock slips straight back inside her pussy and I start thrusting once more, this time her legs up around my side pulling me in.
Several minutes of thrusting later I can feel myself edging close again but this time I didn't stop and kept going, She could tell I was getting close, I tried to keep it quiet as her mum was asleep across the hallway but a good amount of grunting & noise did escape along with the odd 'Oh, fuck..'
With her hands digging into my back.. It was becoming more and more difficult to hold it back and after a while I just couldn't anymore so with a rather loud 'Ah, fuck' I pulled out, cumming all up over her stomach stroking my cock as I came. The release felt so good, but I was determined I was going to make her cum too so I slipped my cock back inside her and started thrusting again.
Fingers spreading her lips, playing with her clit with my thumb as I thrusted. I could feel her starting to tense up around my cock.. She's started to pinch her nipples between thrusts, I could tell she was start to get close so I kept going and then after a few more minutes I hear her start to gasp, letting out short breath she starts starts cumming so I push myself as deep as I could, her entire pelvic muscles clenched my cock it felt so good!
We collapsed into each other both heavily panting before gradually I pulled out, and rolled over onto my back. We both laid there for a good while as we caught our breaths. I can't speak for her but I was in complete disbelief, and after a short while we must have passed out because I don't remember much from that point. We woke up the following morning almost like nothing happened, it wasn't until I went to leave a few hours later, just as I was about to get into my car to drive home Emily then comes subtly says to me 'Last night was fun, but we probably shouldn't do that again' to that I replied by agreeing (not really) however several weeks after that night, I then find out from her that she's pregnant with her then ex-boyfriend's baby and inevitably they ended up getting back together so that all but confirmed nothing else was happening from there but I'm never forgetting that night.