Descriptions:
I’m 5’10”, 175lbs., in pretty solid shape at the time of this story. I had short, dark, “styled” hair and was generally considered a pretty good looking guy.
Stacy was about 5’2″, 95lbs, absolutely tiny frame that somehow had perky b-cups, very cute face, and shoulder length “blonde” hair.
Background:
I had grown up with Stacy from when we were in elementary school. Our mom’s worked together, were great friends, etc. I’m almost exactly 1 year older than her a grade ahead, so we didn’t really hang out much but we knew each other well from seeing each other in school and when our moms would get together.
Years pass with us knowing each other, being friendly, but never really being friends until we start working at a local casual dining restaurant together. Within a few weeks, all that time and knowing each other exploded into full-on best friend status. All the background knowledge we had, the shared experiences, the inside jokes, all came together to make this incredible, platonic relationship. We hung out all the time outside work. We were both in high school when we started working there, so we’d hang out between classes, with overlapping circles of friends. We would approve or disapprove of each other’s dates. I mean, pure, platonic friendship at its finest.
We’re both fairly attractive, so we typically didn’t have trouble finding dates or hook ups and, if one of us ever struck out, the other was their to play wing man/woman. We talked about sex often, but always as curiosity and just general friend banter about what’s going on in your sex life. It’s important to emphasize that in over a decade, neither of us had made even the slightest move toward anything physical happening between us.
Lead in:
Shortly after I graduated and she was freshly 18, we were hanging out with our friend group for our shared birthday weekend. This friend, Sandy, had the “cool” parents, so they had a room upstairs across from Sandy’s room that the rest of us slept in when we got together to make sure no one drove after drinking.
Stacy had her regular fwb coming over and one of our friends, Tina, had just ended things with her long-term boyfriend. Well, Tina decided that tonight was the night that I was going to fuck her. The night carries on not unlike other weekend nights for us, we all get a little drunk off Sandy’s parents’ booze, some of the older friends drive home “since they’re legal,” and the four of us are left hanging out. Tina is getting pretty handsy at this point but she’s never been much of a drinker so she’s also a little bit sloppy drunk.
It’s getting late, Susan’s dude never showed up, we all decide to call it a night and go upstairs. Sandy goes to her room, Susan to one bed, Tina and me in the other bed. The lights aren’t out good and Tina is passed out. So, Susan and I are both laying awake in the same room, just talking. We decide that since neither of us hooked up, let’s have another drink and play some PS2. We play the game and snuggle, which is pretty common for us. About an hour later, we decide to turn it off and go to bed.
The Action:
We get in bed together; she’s wearing some tiny, cotton shorts and a halter top. Cute, not super sexy, but easy to remove in anticipation of her dude coming over. I strip down to my boxers because I’m going to bed and I’m sure as shit not wearing a bunch of clothes! We chit chat a little more, lament how we both didn’t get anything tonight and how we both really, really had wanted to. Again, this wasn’t abnormal.
We’re cuddling a little, kinda rubbing each others’ backs and I hit a tickle spot on the small of her back. She jumps and says not to do that. So, of course, I go “what, this?” and graze my fingers across the small of her back again eliciting another jump and “quit it!” response. We go back to petting each other with me teasing around the area, her levying empty threats of “don’t do it, you better not,” etc. Being 18 myself, of course I did it more. What I didn’t know, however, was that this wasn’t really “tickling” her so much as it was turning her on.
She finally tells me why I need to stop, that it’s driving her wild and she was already frustrated enough. It’s late, I’m immature, and maybe my dick was doing a little of the thinking for me, so I would keep gently grazing my fingers across her.
“Alright, you want to play dirty?” She rolls over on top of me, pinning my wrists beside my head. “What do you think of this?” She starts grinding against me, instantly bringing me to a full erection (oh to be 18 again). She’s trying to be sexy, but I just can’t see her that way still. Don’t get me wrong, I’m hard as a rock and it feels great having her tight, lithe body sliding up and down my cock, but looking up and seeing *her* made it almost funny.
She rolls off and says something to the effect of “so don’t do that anymore or I’ll have to do *that* again.” We go back and forth with this a couple times and she’s on me again, hands on my shoulders, really grinding into me. “If you don’t leave me alone you’re going to have to do something about this. Is that what you want?”
I honestly didn’t even think about it. It was such a foreign concept to me that something would happen between us so I keep things going. I “retaliate” by running my hands up her sides under her shirt. The tickle this time causes her arms to collapse and she falls across my bare chest. She moans a little and I run my fingers along the edge of her shorts in the back, holding her down against me. She’s writhing her hips in small circles.
“Ok, you asked for it.” She slides down my body and starts kissing along the inside of my hips. She slowly starts to peel back the elastic on my boxers placing a kiss on each newly exposed bit of skin. She gets the shorts down as far as they’ll go with me laying on them, reaches under me to grab the back. Instinctively, I lift my ass. “Uh huh, that’s what I thought” and she goes back to kissing along my legs.
She wraps her tiny hand around my cock. I’m average length but very thick and uncut. We’ve never seen each other naked before, either. She strokes my shaft while working her mouth closer and closer. She licks from the top of my balls up my shaft, locks eyes with me when she gets to the top, and licks a circle around my head before wrapping her thin lips around me and sucking me deep into her mouth. It felt incredible and she was truly amazing at it.
Not to be outdone, I grasp her face and tug her up to me. We start kissing for the first time and I roll her onto her back, cupping her tight little ass. I slide from her lips to her cheek, nibble on her ear like she’s told me she loves, and kiss my way down her neck. I hold her sides and she lifts up enough for me to pull her shirt off exposing the two most perfect tits I had ever seen. They were firm and sat right in the middle of her chest. Her pink areola were already stiffening, presenting the perfect little buds of her nipples to me. I sucked one into my mouth while squeezing and massaging her other, then switched and continued my journey down her body.
I established a nice, cozy spot on my belly between her legs. I kissed along her hips how she had done to me, squeezing her ass and sliding her shorts off. She lay there, in only a very tiny thong, breathing heavily, running her fingers through my hair. I traced the edges of where the material met her skin while gently kissing and licking along the inside of her thighs, progressively closer to her soaked pussy. The fabric was wet all the way to the edges by this point, so I knew she had to be absolutely dripping wet underneath. I pressed my lips against her with my mouth open, just breathing for a moment, letting out a low hum. She arched her back and pulled my head in. I could hear her faint “please… please…”
She was wearing those thongs that have the clips in the front. I wasn’t familiar at the time and gave up pretty quickly opting to try to sexily slide them off over my head. When that failed, I tried to rip them off. She put an end to that immediately and simply unclipped them for me. The front fell down, exposing her shaved slit and landing strip down the middle. Her outer lips were swollen and her pink, inner lips were poking out. She was glistening wet from the top of her clit all the way down between her cheeks. Picking up where I left off, I continued to lick along the creases between her legs, the edges of her lips, then slid my tongue into her hole while brushing my nose against her stiff clit. She jerked at the contact and moaned loudly. Tina suddenly popped up out of bed. Shocked, I dove back up beside Stacy, pulling the covers over both our naked bodies. Tina had already covered half the room, grabbed her purse, and quickly walked out the door to go to Sandy’s room.
We laid there for a minute, frozen, before laughing at how awkward that had to be for her. In hindsight, dammit I wish she had spoken up! They’ve played together before and that was the PERFECT situation for a threesome! Alas, it never happened. We cuddle some more, a little taken out of the mood. Cuddling leads to petting; petting quickly leads to touching and kissing. She leans over me, sliding on top. She reached off the side of the bed and pulled a condom out of my pants pocket. She slides back down my body, taking my semi-erect dick back into her mouth. As soon as it’s hard, she puts the condom over the tip and rolls it onto me with her mouth. She takes a few more strokes with her mouth and hand before climbing on top of me.
Apparently, she never lost a beat from being interrupted. I, however, was taken firmly back into the reality that I’m not hooking up with some hot girl; I’m hooking up with my best friend who’s felt more like a sister for years now. She slides her slick slit over my cock, does this awesome little move with her hips that vacuums my tip up to her entrance, and slides down me moaning. I literally feel her tremble on top of me when she settles down in my lap. And that’s when I lose it. I’m looking at at her amazing body, squeezing her tits, feeling her impossibly tight pussy wrapped around my cock, and I look up to her face to see her ecstasy. Instead, my mind just sees my best friend and my dick decides to bail on me. Almost as fast as I got hard, I go soft. Not semi-soft like you could still work with it, soft, shriveled, sliding out of the condom, soft.
She just looks down and goes “what the fuck, man” before sliding off. Like a trooper, she tries to resuscitate my erection with her mouth. Having her face out of the equation, I get hard again. I push her onto her back. She spreads her legs wide with them in the air. Her pussy is wide open for me. I push in; heaven. I can’t remember a tighter pussy. Her walls are just so strong; she’s squeezing me as I push into her. Her body is so tiny, I feel her cervix before I’m all the way in. Again, her head is tossed back and she moans my name. And that ruined it. I keep plugging away in vain, but I’m soon too soft to penetrate her.
Embarrassed, I dive back in with my mouth. She’s fine with this turn of events and expresses it by digging her nails into my scalp with one hand, bracing against the arm rest of the futon with her other hand, arching her back off the bed, and moaning loud enough that everyone in the house definitely knows what’s going on if they didn’t already.
I know she’s already getting the girl version of blue balls, so I go straight to her clit this time. I pucker my lips like I’m giving it a kiss and gently suck her while flicking the tip with my tongue. She writhes against my face, trying desperately to get more contact. I ride her out a little longer, then start taking full, long licks from her hole up across her clit. This elicits a deep guttural sound from her. She spreads her legs wider and grabs my ears. I take her cue and wrap my lips around her again, but more broadly. I suck in enough to pull on her clit and begin swirling my tongue around it. I pushed me middle two fingers in and out of her, then did that “come here” motion when I felt her getting close. Her orgasm erupted through her body. She squeezed her thighs around my head, locking me in place and pinning my hand down. She thrust up and down off the bed with her hips, grinding her clit against my tongue and my fingers in and out of her. I could feel her walls pulse and contract; her whole body shook with each crashing wave. As it began to subside, she gripped my hair to pull my head back and get me to stop licking. I continued to finger her more slowly until she said stop.
I climbed up beside her and she snuggled right into my chest, panting. I held her for a while until she caught her breath. She told me it was the best orgasm anyone had ever given her, and that included a lot of girls, too. She told me how intense it was and how special it was that it was me who did it for her. We kissed again and she placed rolled over to go to sleep.
What the fuck? No! Now that I’ve made her cum, and cum hard, my dick is tooootally fine with her being a sexual person to me. I’m throbbing hard now, but I feel awkward saying anything after already going soft inside her twice. So, I lean in and spoon her. Of course, I’m insanely horny at this point, so I start playing with her boobs and my dick is poking her butt.
I manage some meek request that I still need to get off and would she please do it for me. She reaches back and starts giving me a very nice handjob. It was pretty hot and I kept squeezing her tits and started thrusting into her hand. I didn’t have another condom but I really wanted to fuck her at this point. I don’t remember exactly what I said, but it was something along the lines of “I really want to be inside you right now.”
She rolls over and gives me a kiss. “Sure sweetie.” She smiles while still stroking me and slides down my body. She wastes no time this time. With her left hand, she slides back my foreskin but not too tightly, grasping the base of my cock to hold it back and keep me in place. She licks around the head a little and starts working her way down my shaft. Her right hand tickled my balls for a moment and crawled its way to my inner hip. I had never had my prostate played with before, but she started pressing in right over my pubic bone. Her right hand making circles in time with her mouth stroking up and down my cock. Every other girl had always used their hand and mouth together, so this was a brand new sensation of having my cock sucked. Her left hand gripping my base, started massaging my balls a little, too. This was incredible. She didn’t ever get me into her throat, but her left hand was strategically placed at the point along my shaft where her lips reached. She was twisting her head while going up and down, sucking me tightly, stroking her tongue against my tip continuously. It didn’t matter that it was *her* doing it anymore. In fact, it was better because it was her now. I started moaning her name, saying how amazing it was. I warned her that I was starting to get close. I felt her hum “okay” without removing her lips or breaking her stride. She kept the same, perfect pace and never lost beat while massaging my prostate. I felt it there first. The tension of my pending orgasm. I told her I was about to cum. More to the point, I panted out “oh God, oh God I’m about to… I’m gonna cum.” She kept sucking and rubbing. I felt this explosion start from low in my belly and erupt from the base of my balls up through my shaft. I could feel my cock jerking against the roof of her mouth as she kept sucking me, trying to keep me in place. A lot of girls will simply catch the cum as it spurts out, but she helped it along by actually sucking it out of me. I could feel the negative pressure of her pulling my cum up my shaft and out the tip. Each up stroke resulted in a large shot of cum into her mouth, followed by her swallowing on the down stroke. She timed her strokes now to go along with my spasms and slowed down to match the decrease as my orgasm subsided. Still, she stayed latched onto me, sucking me without moving her head. She pulled the last drops of cum out of me, licked around my shaft and head to clean me off, and finally let me fall from her mouth.
She took her place back on my chest and I held her while catching my breath this time. I told her how amazing it was and how I never thought of her that way before but how incredible the experience was. We kissed some more and decided easily that we were absolutely not going to pursue a relationship but maybe we could mess around from time to time. We never so much as kissed again, but we stayed best friends for years to come after that. What I wouldn’t give to have been able to fuck her, though.
Source: reddit.com/r/gonewildstories/comments/5azqdq/best_friend_backup_plan_mf_teasing_oral
Who is Susan?