[Group] My best friend watched me receive oral, then cuddled me as I orgasmed

Kate is one of my best friends. We met in one of those bizarre, fated kind of ways. We happened to go to a board game bar at the same time because we both home from college and feeling lonely. We got paired together, started talking, and suddenly three hours had past before we had even opened the box. We left to grab food, and I invited her over to hang out more afterward. It’s New Year’s Eve, and she invites me to a new age-y New Years party that she got roped into going to with her mother. It was a hell of a good time, and we sat together at a bonfire and talked about everything from philosophy to kinks to emotional trauma. By the time we stopped hanging out that first time, 33 hours had past, we had slept on a couch together, and we nearly had sex.

In the two years between meeting and this story, we continued to be incredibly intimate and continued to not have sex. We have slept in the same bed often, are not shy about telling each other we love each other, and have platonically kisses on the lips once. But it’s the kind of deeply intimate relationship where adding sex inorganically would almost cheapen it, if that makes sense. If we decided in the moment we really wanted to I’m sure we would, but that hasn’t happened yet and I don’t particularly expect it to.

Madeline is my girlfriend. When this story occurs, we are in an open relationship. Emily is 24, 5’4,” 105 lbs with dirty blonde hair in a pixie cut she would have a textbook hour-glass figure except she cut all her boobs off, so instead she just has a crazy hip-to-waist ratio and what she affectionately calls “hand sized boobs.”

Kate is 23, 5’4”, 120 lbs with shoulder-length dark brown hair and warm brown eyes. She has a major “sexy librarian” or “sexy philosophy TA” vibe going that I’m hugely into, both personally and sexually.

I am also 24, 5’7”, 140 lbs with ringlet brown hair that goes to my breast. I have piercing blue eyes that regularly cause people to ask me where I get my colored contacts from. My best physical features are my ass which is firm with just a little wiggle to it when you slap it and the muscled physique I got from rock climbing (or used to have – grad school caused me to drop the ball there and I haven’t gone climbing much recently. Actually, the day I wrote this was the first time I had been in over a year.) My aesthetic is anything that matches my Doc Martins and leather jacket (both of which are black, duh!)

So Kate comes over to stay with us for a weekend and after dinner and desert we change into PJs and hop into bed. Madeline is wearing full body PJs, while I am topless in silk bottoms and Madeline is wearing panties and a t-shirt. We have a king sized bed, with Madeline on one side, me in the middle, and Kate on the other. I cuddle up into Madeline and the three of us talk until Madeline starts to fall asleep. As she drifts off she clutches me tighter and Kate remarks on how cute my girlfriend looks, clutching me like a teddy bear.

Kate and I continue to talk until I suddenly feel Madeline shift, her hand drifting into my pants. I freeze, but Kate is on her back looking upwards and doesn’t seem to have noticed anything. As Kate continues to talk Madeline begins to stroke me, first gently and then with increasing vigor. I gingerly test to see if Madeline is awake and am surprised to realize she isn’t. Although Madeline has no compunctions about sex in front of others (we once had a threesome with a coworker of hers because she decided to start giving me head while we were hanging out and drinking), sleep sex was a new one for us.

Over the next half hour, Kate and I continue to talk as I become increasingly horny. I’m the kind of girl who can only orgasm from a handful of specific types of stimulation, and manual stimulation doesn’t do it for me. I decide to clue Kate in on what’s been going on, partially out of a desire to share and laugh with her and partially because I’ve started to get it in my head that not only do I want to orgasm, but I want to orgasm in front of her.

Kate doesn’t believe me at first, so I pull back the blankets to reveal my PJs at my knees and Madeline’s hand having its way with me. As I do so, I release my breath for the first time in half an hour and begin to moan softly. Kate stares at my crotch, then at my face as I begin to let myself get more and more into it. I reach out and take her hand, and we lie there holding hands as I moan.

We check in about comfort and boundaries again, and agree that I would get myself off and then we’d go find a vibrator for Kaitlyn to use on herself. I extricate myself from Madeline grip and take my pants completely off, touching myself briefly while looking at Kate. The way I masturbate to orgasm involves pressing something soft but firm (typically a pillow) into my crotch and rubbing, but I get a slightly different idea watching Kate watch me. I instruct her to lie on her back and move over so that we are spooning, but facing each other. I force a pillow between my legs and take Kaitlyn’s arms and wrap them around me.

I close my eyes and begin to masturbate, picturing a crazed foursome involving the three of us and a faceless boyfriend of Kate’s. The image that has stuck with me is the picture of myself going down on Madeline while Kate rides her face and her boyfriend fucks me. It’s a scene I’ve gotten off to many times since. I open my eyes and tell her I’m close, and she takes my hand while I clutch my legs around her waist and ride myself so close to orgasm. Our faces are so close that our lips are touching, and I briefly consider kissing her. But the strangely platonic nature of the interaction gets to me and I don’t want to break it. She breaks the silence by saying “come on, be a good girl and cum for me” which immediately sends me over the edge and I gush and convulse, clutching her.

After some time we go hunting for a vibrator. Unfortunately both Madeline’s vibratory and the guest vibrator are dead and so we plug them in and get back into bed. I offer to get her off, but Kate demurs and we fall asleep quickly.

The next day is pretty typical, and Madeline is blown away when we tell her what happened. She has zero memory of any of it and has never had anything like that happen before (though as we’ll see, it’s not the last time!). The rest of Kate’s visit passes without anything out of the ordinary, and our sexual escapades don’t make anything weird or different between us. The one thing it changed was that it planted a seed of desire to do voyerism / exhibitionism stuff in front of Kate specifically, which I continue to fantasize about two years latter.

Source: reddit.com/r/gonewildstories/comments/srz6rc/group_my_best_friend_watched_me_receive_oral_then