This is the story of how me and my best friend lost our virginities - but not to each other...
Dayna and I knew each other practically our whole lives - at least since kindergarten.
She came from a from a fairly large family - 4 girls and 1 boy. There was Natalie, the oldest and two years older than Dayna, and then Amanda, only one year older. Dayna and Ryan were "Irish Twins", born 10 months apart in January and October, respectively, and so were always in the same grade. Bailey settled in as the youngest, three whole years after Dayna and Ryan. The 3 sisters have stories of their own, for one day, but Dayna was always the one who remained in my life. A complete mutt of European heritage, her mom's side was French and Italian, and her dad's was generic British Isles before moving the family to Canada generations ago. Dayna captured fairer features than most of her other siblings, with straight, thick, golden hair, paler, flawless skin, and almond, hazel eyes. Short.
As young kids, I met and grew close to Dayna, but then as we got older we sort of hid our crushes from each other as I grew a close friendship with Ryan and "ew, no way I'd like your sister, man!" But then once the idea of cooties calmed down, Dayna and I became best friends again. We were each other's confidants, telling each other about our crushes and first kisses, as well as each other's friendly rivals, competing for marks in school, teasing and gently flirting with each other. We'd go swimming and I'd take in eyefuls of her bikini body when I though I was being sneaky. That sort of thing; but we only ever stayed what we were, best friends.
This catches us up to the summer after graduation.
We were both 18 and virgins, but honestly, I didn't really care. I'd fooled around with a few girls by then and had just started casually seeing a new girl who was pretty frisky and adventurous, and it only felt like a matter of time.
That summer we were out at a house party of a mutual friend. I was with the new girl I was seeing, Jessica, and Dayna had hit it off with a friend of a friend who we only previously knew in passing, but seemed alright, Andy.
The drinks are flowing - not wild, just loose enough - and at some point the four of us are hanging out in the living room, chatting and drinking. As the conversation grows long, Jessica is getting a little drunker, a little flirtier, and a lot handsier.
Eventually Jess starts grabbing and caressing my junk through my jeans. Still to this day, I don't actually know if my Dayna saw that, but it was still an incredibly hot experience getting worked up and felt up with Dayna right there. Eventually, Jess whispers in my ear that she wants to go to a bedroom.
I pretty quickly excuse us, and Jess, tipsy, makes a bit of a show of it, "accidentally" flashing her ass in her skirt to everyone as she is getting up. Dayna and Andy laugh as Dayna gives me a wink and a smile of encouragement and mouths, "Good luck." Then, as I stand up too, Andy much less discretely asks Dayna if she wants to find their own room to go to.
Dayna, now slightly red in the face, makes only very brief eye contact with me this time - but only in a way to kind of acknowledge, like, "I won't judge you if you don't judge me", and takes his hand.
All four of us head upstairs to find SEPARATE rooms.
Jessica and I get upstairs and get into the first unlocked bedroom we could find. It's a smaller room with two twin beds on either side of the room. It's a younger sibling's room of the mutual friend's house we are in, and the family was all gone for the week and our friend knew we'd all be crashing, so it doesn't feel that weird to be setting up in the bedroom.
Not even 30 seconds later, though, the door opens and it's Andy holding Dayna's hand behind him. He quickly apologizes and mentions all of the other rooms are taken.
Now, I should add here, Jessica knew full well of how close Dayna and I were and Andy had had it explained throughout the night too, but now he quickly sees the two beds in the room and declares, "Perfect!" and pulls Dayna into the room with him.
Dayna and I make brief eye contact again, but she doesn't protest. I think we both think, "it's not like it's going to go that far", as Andy pulls her eyes away from me and begins making out with her on the bed opposite us.
Jess is shortly all over me and we each make out in our own couples on either side of the room, ignoring each other for a few minutes. As this continues, Jess' top comes off pretty easily and quickly, and I'm really not looking (or, frankly, explicitly interested in what's going on on the other side) but Dayna's top quickly comes off too after that.
I'd of course seen Dayna in a bikini, and a couple of nights of drinking and games over the years, she'd flashed her bra. She had nice soft but perky C cups, not spilling out everywhere, but definitely a nice shape to admire, even with a shirt on, but now here she was in black jeans and a black bra against her milky white skin, and her eyes are closed as this guy's kissing all over her stomach and chest. All while my girl is grinding all over me, and I'm now suddenly topless too.
Andy moves his hands to her pants, undoes them, and begins to pull them off. It's quick and she's in her bra and panties. Nothing more. She's not flaunting it, but doesn't seem uncomfortable, not one bit.
I take this as permission to take Jessica's pants off too to reveal a nice, round ass, much fuller than Dayna's, but pretty much most of Jess was fuller than Dayna - ass, breasts, thighs.
What happens next happens fast, and largely unexpectedly.
Jess positions herself in between my legs and in pretty quick succession, she undoes my pants, tugs at my jeans, and then pulls down my boxers exposing my rock hard cock.
It happened so fast, I legitimately didn't even process what was happening until I was out in the air.
Dayna didn't acknowledge it or make any new noise or sudden movement. She didn't look to make eye contact with me or anything, but she definitely saw it, there was no way to deny that...
But almost without missing a beat after her eyeful, she spins herself around so her back is to me and my cock and I could see her thong-framed ass as she settled between her own guy's legs, takes out his cock and starts sucking it.
I couldn't see her mouth, just the back of her head as she went down on him and my girl started going down on me.
It goes like this for a solid period of time, the two girls sucking cock. I try to stay pretty silent, and keep my eyes on my own prize, but the occasional slurping noise on the other side of the room is driving me way more sexually charged than I would've guessed. I think Andy must see my occasional wandering eyes, though, because he eventually twists their bodies slightly so that I can catch a side profile of her going down on him.
Fuck.
I almost bust right then and there.
After what feels like an eternity (though I think it was only a couple of minutes) of seeing my best friend - the girl I had grown up with and pretty much accepted would only be a lingering hug and fantasy fap at best - swallow this dick while my own was being worked on, Jess pushes me onto my back on the bed, pulls my pants the rest of the way off so I am completely naked and begins stripping herself down.
First her bra. Large, heavy set E cups that only look exaggerated by her relatively small waist with sort of surprisingly smaller, light brown nipples. Then her thong. Short, stubbled fur atop a vulva that hides her clit when looking front-on.
This catches Dayna's full attention and she stops sucking, cock in hand, to turn her head and watch as Jess' naked body straddles my midsection, and I watch her eyes as they flutter up and down our naked bodies - my naked body - pausing slightly, at least in my memory, at my exposed cock sitting just behind my Jess' round ass, before she herself stands up and says...
"Okay, but this next part is happening UNDER the covers!"
It's a little sheepish, a little impish, and entirely hot.
I silently agree and pull the covers over Jessica and me and then flip her onto her back.
Dayna climbs under her own covers and I see a bra reappear and land on the floor, followed by her panties. She's holding the covers skin tight to her body for some modesty. Andy sets up for missionary and they make out for a bit.
This is my first time too, so I bring the attention back to Jessica. She's incredibly wet and eventually I slip into her with complete ease, and I'm mostly blind to the rest of the world as I get my dick actually wet for the first time.
Feels fucking good.
I stay this way in my own world until I hear a soft gasp from across the room. He's entered her. I can't help but steal a glance over and their bodies are under the cover, but her face is in equal parts unsure pain and pure bliss. And then they're fucking.
And we're both fucking.
If I thought her slurping was gonna get me... my god, her moans. Her moans. I will never forget those noises.
Both parties are having a good time, doing their own thing, and the pace is getting faster, but slowly, through the course of fucking, the covers slip and her tits are exposed.
I don't actually know how long they were out before I noticed, but she seemed to have told herself "fuck it" at that point as she wasn't pulling the covers up to fix it.
They're PERKY, bouncing back and forth with their rhythm, extremely different but equally as captivating as the larger soft breasts flopping back and forth beneath me.
The sight encourages me to care less as the covers slip down my own body and eventually I can feel the fresh air on my ass and know I am totally exposed, fucking this girl next to my childhood friend.
Dayna's breathing is heavy and her face is deep red and next her covers slip all the way off, too. Once again, maybe it's just my creative memory filling in the gaps, but I swear I remember seeing her legs kick the blankets for that final push...
Either way, there she is. Her legs... her bare hips... her ribs... her breasts... her closed eyes... her face of ecstasy... her guy pumping in and out of her.
I make the next move, flipping my girl over and positioning her for doggystyle, honestly, largely so that I could a better view of both situations at the same time. And during that transition, my cock is out for all to see. If Dayna cares at this point, it is in a supportive way as she is watching as I thrust into my girl from behind for the first time.
