I [f]ucked my best [f]riend and took her virginity

This took place a few years ago, but I’ve wanted to write about it ever since.

To introduce myself, I’m Alex (not my real name for obvious reasons). I’m bi and I’ve been out since I was a teen, and I’ve been best friends with Kasey (fake name too obvs) since early high school.
I used to be a bit overweight but I slimmed down a bunch at uni, and I’ve had short hair forever. I’m also tall and admittedly pretty confident, so I’ve been relatively popular with both ladies and guys since early adulthood – nothing ridiculous, but definitely capable of hooking up with whatever gender I want when I go out. Kasey is pretty curvy, and only came out as bi after high school. She’s pretty cute – I think I had a crush on her for all of two weeks when we were about sixteen, but never any serious feelings or attraction – but quite shy when it comes to dating or making a move on anybody (and a virgin when this happened). In fact, only a couple of months before this encounter, I learnt she’d never had an orgasm – something unthinkable to me, who’d been jerking it on the regular since I was young due to a high sex drive. We went to a sex shop and I helped her pick out a vibrating dildo. At first she couldn’t quite get it to work, but when she did … she thanked me a lot. ;)

So back when this all happened, I was about six months fresh off a really shitty breakup with my first ever long-term boyfriend. I’d also only had sex for the first time maybe two weeks before we started seriously dating, so when we broke up I’d only ever had sex with two people.

I’d never really considered myself a hugely sexual person before then, but shock horror! It turned out I fucking loved having sex. I loved feeling sexy, I loved blowing guys, I loved kissing everyone, I just loved every part of it. So when we broke up, I went into a pretty slutty phase for a while. Not so slutty as some of the stories I see on here, but still enough that all somebody needed to do was go out on a couple of dates with me and I’d gladly be on my knees sucking the life out of them.

So, onto the fateful day. As luck would have it, Kasey and I were both single at this time and thus pretty bored, so I went over to her house when her parents were out to get drunk and watch a movie and chat. She’d also never smoked weed so I brought some over for us to get a bit stoned if she wanted.

We sat on the couch upstairs talking for a while. Before long we busted out the weed, but hilariously we were so terrible at rolling joints that she wasn’t able to get high, and she also wasn’t feeling the effects that much so she started on the alcohol. Meanwhile I kept going and pretty soon started to feel super high. Not quite baked as fuck kinda high, but the pleasant sort of high where I’m spacing out and everything feels awesome. Kasey downed a lot of whiskey in a short amount of time, so she was drunk pretty soon.

So we’re sitting on the couch, Kasey’s pretty drunk and I’m pretty high. I don’t remember how we got onto the topic, but we started talking about same-sex crushes at some point. I don’t remember a lot of what we said that day, but I could never forget this, because she looked up at me with this ridiculously smouldering, intense look, and said,
‘You know, I used to have a crush on you.’
I smiled, surprised, probably looking like an idiot because I was stoned. ‘Really?’
‘Yeah,’ she said, and then the next thing I knew her mouth was crashing into mine.

I was high and pretty out of it, but I haven’t forgotten what it felt like to have her mouth against mine. I remember thinking about how weirdly small her mouth was, being mostly used to kissing guys, and almost laughing out loud at that thought. Her tongue was pressing into my mouth, hungrily, like she’d wanted this for a long time. I pressed back, my hands eventually falling to her waist, and we made out on the couch like that for a while. I was a bit dazed because I’d truly had no idea she’d ever had a crush on me let alone the fact she was still – apparently – attracted to me. But I couldn’t deny I was enjoying it. It’d been a while since I kissed a girl and there’s something deeply hot about it, something different to being with a guy – they’re so soft, so curvy, and they smell so damn good.
We kissed furiously for a while before finally she pulled away and said, ‘Should we go to my room?’

I think I just nodded. She led her way to her bedroom and I followed after, stumbling slightly. I was very much in a daze, part confusion, part arousal, mostly *I’m going to have sex with my best friend holy shit.*

It was pitch-black in her bedroom since she had the blinds drawn and we’d obviously sat around talking for longer than I realised, so she pulled me to her bed in the dark. We fell onto it and our mouths connected again, except this time everything felt even more frenzied.
I was on top, trying my best to match her frantic kisses, and I made her shimmy up so I could take off her top. Something great about Kasey is that because she’s pretty curvy, her boobs are huge. I’ve only ever been a B-cup, so I was kind of amazed at how big they felt. I gently squeezed them through her bra as we resumed kissing.
It’s hard to describe how I felt then. I’d actually never had sex like this with a girl before, and I’d never really had a deep crush on Kasey. I’d been eaten out by a girl before, but I’d only fantasised about eating out a girl before (a ton, admittedly), and now that it was going to happen, it just felt so bizarre that it was with my long-time best friend of all people. Above all that, though, I was enjoying this a ton, and the weed had helped to cut out some of the nerves.
As I kissed her and ran my hands over her body, I also realised how much I liked the idea of being dominant. It was a hot feeling to have a girl beneath me panting into my mouth and bucking against me, a hot feeling to be in charge and to be the one who was going to give her an orgasm. I don’t have the words to describe it, except that it was just insanely fucking hot.

I shimmied her pants off and she undid her bra, and then suddenly she was naked beneath me. We didn’t have the lights on, so it was all touch, and it made it surreal in a way. We were still frantically kissing, so I started kissing my way down her body, sucking on her nipple as I did, listening to her moan, until finally my head was between her thighs.

That first press of my lips against her clit was heaven. She was dripping wet. She tasted like salt and sweat, but somehow sweet too. I licked long and slow from her hole to the top of her vag, and smiled when she moaned loudly and grabbed my hair. I pressed my face into her folds, licked hungrily, and was rewarded with a pull on my hair. God, her pussy tasted so good. She squirmed beneath me, whining. I realised her pussy had been recently shaved – had she been planning for this to happen? – but the thought left my head pretty soon.

I positioned my mouth so my tongue was able to flick back and forth quickly at her clit, like a dog lapping at water, and alternated that with long slow licks up and down her folds. Eventually I wanted more, really wanted to send her into overdrive – she’d mentioned something ages ago about how internal stimulation really made her get off, so I lifted up a finger, sucked it, and slid it inside her.
To this day I won’t forget how good she felt. So tight, so warm, so fucking wet, her pussy muscles clenching and unclenching around me, and soon I added a second finger, slowly pumping them in and out while I buried my face in her pussy and licked her clit.
She was moaning a lot by this point, and at one point I stopped to kiss my way up her body. She grabbed my face and kissed me hungrily, while I kept fingering her.

After a second she told me to wait, and I leant back. She twisted to the side and I heard her fumbling in her drawer. She pressed silicone into my hand and I realised it was the vibrating dildo I’d helped her pick months ago.

I leant over her, her breasts pressing into my chest, and kissed at her neck while I slid the dildo inside her. She grabbed my shoulders and curled her legs around me, groaning as I slowly slid it in and out. At one point she whispered to me to go faster, so that’s exactly what I did.

I’ve always had strap-on fantasies and had the good luck to fuck a couple of guys that way, so I knew what I wanted to do. I leant back up so I was kneeling between her thighs, her legs spread wide, and positioned the dildo so it was sitting in front of my crotch, the tip of it just inside her. And then I slammed my hips forward.
She gasped and arched her back, and that was worth it. I pulled my hips back and fucked her like that, going deep inside her. God, it felt good. I felt powerful and dominant and revelled in the way she moaned and whined and begged for more beneath me. All it made me do was fuck her harder, until she was nearly yelling. I leant down when she was getting a bit too loud (her younger sister was home and in a nearby bedroom, awkwardly enough), but she promptly told me she didn’t give a shit and pulled me in for a kiss. I fucked her like that for a little while, but the angle made it awkward.

I slid down her body and pressed my lips against her pussy once more, kissing and sucking at her folds and pressing my tongue flat against her clit, but the dildo was awkward to use at this position, so I took it out and settled for thrusting two fingers in and out of her again. She was clenching and unclenching at a faster pace, and she must’ve been close. I quit licking her clit for a moment to kiss her again, but she immediately gasped and told me that *oh god I’m about to come, please, please,* and I ducked my head down again to lick furiously at her clit and hammer her with my fingers.

The feeling of her coming on my fingers and my mouth was glorious. She yelled out and bucked her hips and grabbed my hair ridiculously tight and I kept fucking her through it. She was sopping wet and her pussy – oh my god, it was incredible – tightened around me so much it was like my fingers were caught in a vice. A warm, wet, vice that clenched and unclenched around me with each wave of her orgasm. She came for a long time, and I slowed down my licks and my fingers until I was gently lapping at her juices.

Finally she pulled my head away and pressed me onto my back, started to kiss her way down my body.
What happened next is hard to explain, but I was still stuck in such a dominant mood and I’ve had bad experiences with people eating me out – I didn’t want her to feel awkward if she couldn’t get me off – so I gently brought her head up to mine and we kissed. I told her it was fine, I was more than happy that I got her off – and that was true.
For a while we just lay there in the dark, her head on my chest – which felt dominant too in a lovely way – and finally we talked. She said how amazing it’d been and confessed she’d wanted to do that for a long time. I admitted it’d been great, but unexpected. At this point I was coming down from my high so I was pretty sleepy, and we wound up just cuddling and watching youtube on her laptop until we fell asleep. In the morning I woke up alone – I felt a little weird but it wasn’t totally unexpected from Kasey, and when she came back (she’d had to take her sister someone for something), we chatted awkwardly and I left.

And unfortunately that’s where my story ends. Our friendship was a bit distant for a few weeks, but she started dating a guy soon after, and I started dating someone else, and eventually we got over the awkwardness and we’re still best friends. She has confessed to me, however, that to this day I’m the only person to have ever successfully given her an orgasm ;)

I never had any experiences quite as hot and slutty as that again, and now I’m in a very loving long-term relationship so I doubt I will for a while (if ever, hopefully). But I have to admit that when I’m getting myself off, one memory I revisit a lot is of Kasey’s wet pussy on my tongue, and how tight and warm and wet she felt, clenching around my fingers.

Source: reddit.com/r/gonewildstories/comments/dt20e4/i_fucked_my_best_friend_and_took_her_virginity