Surprise! How a trusted, yet devious friend [M] fulfilled my [F23] stranger [M] fantasy

I always find it incredibly arousing to read and hear stories about other’s slutty adventures – the more promiscuous, spontaneous and somewhat irresponsible the better. No shocker… I’m a big fan of this sub. One question I always love to ask, and love when others ask me, is “What’s the fastest you’ve gone from meeting someone, to having them inside you?” This is the story of my answer.

If you’ve read [my previous stories](https://www.reddit.com/r/gonewildstories/comments/fppy8e/six_close_friends_in_a_dark_closet_group/), you may know that I’ve developed a knack for going after that incredible rush you feel when a cock enters you (or is shoved in your mouth), and you don’t know to whom it belongs. I’ve been lucky enough to have had a few adventures with a group of friends where either darkness or blindfolds helped to facilitate that type of situation. Still, I always knew it had to be someone in the group. I knew I wanted to take it to the next level, to actually have sex with a true stranger. The only question was how to do it safely, while still keeping up the fun and intrigue.

***

A little over a couple years ago, when I was 23, after a regular session with my friend Matt, who I had been seeing often at the time, I was ruminating on new situations or things we could try together and I brought up my desire to fuck a complete stranger.

*”I’ve always loved not knowing who is inside me, and I’ve certainly gone from 0 to fucking pretty quickly in the past, but I’ve never not known or seen the person before we actually get down to business, and I’d like to.”*

Matt responded by saying he could do me one better – not only could he help arrange for a stranger to fuck me, but if I was open to it, he could make *when* it happened a complete surprise as well. I almost came again as the words left his mouth. *”Yes. God Yes.”*

“Do you want any more details? Any rules? Preferences?”, he asked. I responded that I trusted him, that he knew me and my comfort level generally, and that the less I knew, the better this would be. He snickered at me with delight, and I was salivating. We had just fucked 10 minutes before and I could still feel his cum slowly dripping out of me, but he was hard, I was drenched, and I immediately mounted him for round two, my mind spinning out of control thinking about how this would transpire. It was an intense, long and passionate round of sex, with my orgasms driven primarily by this fantasy. If this was how good things were just thinking about it, I shuddered to think about how hard I would come when it actually happened.

Weeks passed, and we had seen each other fairly regularly, but no plans had transpired and I was beginning to forget about it generally whenever we got together. Matt made me promise not to ask him about it, so I kept my word. We’re both quite into teasing each other, and while I may have been slowly losing my patience, I knew he must have had a plan. The fact that we had often used blindfolds and even noise cancelling headphones with music playing to block out all visual and audible senses made it even harder to tell when he planned to execute this fantasy (though is definitely something I recommend trying!)

One night, he asked at the last minute if I was free, I said yes, got dressed, and excitedly headed over. He asked what I was up for, and I responded that I had already had sex earlier that day, so didn’t need the ravenous immediate satisfaction that I sometimes demanded when… starved. We could play around a bit and have some fun, basically.

We moved to the bedroom, and he smiled at me as he took out the blindfold and headphones. I removed my top layer and pants to reveal one of my favorite pieces of lingerie, a black lacy babydoll piece that didn’t hide much of my 5″6, 130 Lb figure – especially considering I was just wearing the top and no underwear ;-) Through the lace my 34Cs were holding their own, my nipples staring pointedly back at Matt’s lips, and my mostly shaved pussy draped with lace, open and warming up to the fresh air.

I laid down, and he put the blindfold & headphones on me, turning on a sensual relaxing playlist not unlike what you’d hear at a spa, but with just a little more “umph” to it. I zoned out as I felt a light feather brushing against my cheek, then down my chest, and around my body tickling me with excitement. He continued with the feather and light touches that slowly began to brush closer and closer to my nipples and clit. The teasing continued for a bit until I felt a warm body of flesh slowly rest itself below my nose, grazing my lips. I licked and confirmed my suspicions, then used my hands to grab Matt’s dick and position inside my mouth. As I sucked, his fingers edged closer down below and then finally went inside me. I’ve never been a huge fan of fingering generally, but I highly recommend trying when you can’t hear or see anything because any new touch or movement has a far more heightened effect when you’re not expecting it.

We switched the dynamics back and forth between me sucking him, and him face-fucking me. While I do have an unfortunate gag reflex I haven’t quite been able to dismiss, I make up for it with a very wet, sloppy, messy blowjob and this was no exception. After quite a bit of this, slobber and pre-cum smothered on my face, the dick disappeared and I anxiously awaited what was to come next. A warm tongue suddenly began tracing up my legs and towards my warm pussy, but just before it got there, it disappeared again, only to be felt again a few seconds later on my nipples, after I felt the light, lacy top being pulled over my head. Things continued on like this, and he continued to eat me out, tease me, and play for what must have been at least 20 minutes and one orgasm before I finally had enough and shouted “Will you fuck me already?!?” I didn’t mean to yell, just tough to know how loud you are when you can’t hear anything.

Almost immediately, I felt the warmth of his tip present itself at my entrance and slowly push inside me. Having just had his tongue inside me and being naturally well lubricated pretty much anytime I’m aroused, he slid right in. We’d fucked a good 50 times before at this point, so he knew all the right moves to make things highly enjoyable for me. He started slowly, with hands all over me, and periodically picked up the pace. He’d also direct me to change positions by grabbing and guiding my body, and I’d let him mold me however he wanted. We started with me on my back, then my side, then he plowed into me as I lay flat, faced down into the covers, my moans muffled by the sheets. We switched positions quite often, including short respites where his cock would materialize in my mouth again.

At one point, I was on all fours being fucked doggy when the pace picked up dramatically and the thrusting became super intense and forceful in the best way possible — I don’t necessarily love super rough sex as a full-body thing, but I do love to be pummeled, and he was delivering. The fucking continued as I squealed and came for what must have been the 3rd time, my mouth open and moaning, and I felt a hard cock being placed in my mouth which I instinctively began to suck. It took about two full seconds before the massive wave of realization occurred and it clicked that there was now a second cock! …and I had no idea whose it was, which one was inside me, or how long it had been there.

I immediately felt a surge of endorphins as two familiar hands cupped my chin, removed my headphones, and lowered my blindfold slightly — just enough so I could see Matt in front of me, grinning at me with delight, his cock in my mouth, as he watched my face express the sheer joy and terror of the realization that I literally had no idea who was inside me at that moment. Matt then looked into my eyes and said “Except for right now, I haven’t touched you in over 10 minutes.” My mind replayed everything that had recently been done to me with the new reality that it had been someone else that whole time.

I started to turn my head to peek behind me, but Matt pushed forcefully back, gestured “no no no” with his finger, and slid the blindfold back on as the fucking continued. My mind raced, and I leaned into the thrusting motions, trying to fully take in this pure moment of ignorance and absolute slutiness. Finally, the mystery man stopped and spoke with a deep voice and an accent I couldn’t quite place: “I heard you like to ride Cowgirl.” I most certainly did.

I heard him lay down on the bed, and Matt graciously guided me on top of him. As I moved my hand to reach down and guide his cock into me, it occurred to me I didn’t know if he was wearing a condom, and Matt and I had never really discussed this — though he knew I put in a commendable effort to practice safe sex when not with known, trusted partners. Not so secretly though, I had hoped he hadn’t been wearing one. The thrill of fucking a stranger only intensified knowing I could be doing it raw. My hand reached his cock, and sure enough, it was skin on skin. I moaned in ecstasy as I guided his bare cock back inside me and began to ride him with a renewed thrill and passion. Matt, standing off to the side of the bed, made sure I didn’t forget about him too and positioned his dick in front of my face, which I gladly accepted – but not before I spoke a muffled “Thank you”, as he stuffed my mouth quiet.

After I came again, we switched positions and while still blindfolded, was laying on the side of the bed on my back, legs off the edge, as my mystery man positioned himself in front of me and entered me again. I felt a hand brush across my face as Matt finally removed the blindfold. I was now staring directly at a beautiful, tall, chiseled man who looked to be in his early 30s, confident and sweaty, watching his thick cock thrust in and out of me. I muttered “Hi there” between breaths. “Nice to meet you”, he responded as he plowed into me.

“I’d like to cum inside you, if that’s alright” he said amusing casually a few minutes later, his hand on my clit rubbing me as he stared into my eyes. Throwing caution to the wind, I nodded in the affirmative as yet another thunderous fervor washed over me and I came again, hard. He stared at me intently as I convulsed and spasmed. When it finally passed and I regained my composure, he shifted me around ever so slightly to enhance my pussy’s grip on him, and relentlessly fucked me, filling up what felt like every inch of me, until he finally groaned with pleasure and I felt the all too familiar pulsing of cock inside of me, and the small gush of warm cum escape and begin to drip out of me as he retreated.

Reminding me I wasn’t done yet, Matt flipped me around and began to fuck my cum soaked pussy as mystery man moved beside me and made me lick what was remaining from his dick as Matt got ready to empty himself in me. Matt came shortly after, and we all collapsed on the bed.

Naked, physically and emotionally exhausted, and with a stranger’s cum spread all around and dripping from my pussy, I muttered: “I’m Jess, by the way.”

“Stan”, he responded.

***

***If you enjoyed this story, I’d really appreciate an upvote or a comment!***

One of my stories finally fit a good contest category and I’d love to win! Happy to respond to questions in the comments.

I also have a few other stories in my profile that you might enjoy. Thanks ?

Source: reddit.com/r/gonewildstories/comments/ne8u4f/surprise_how_a_trusted_yet_devious_friend_m