I’ve known Madi since we cheated our way through 8th grade geometry together, we lost touch during our college years and reconnected when we wound up in the same city after, we’ve stayed good friends since. When we first reconnected we went on a few dates but it didn’t click, got drunk and had sex another couple of nights but there was too much pressure with our history… and honestly I don’t remember much of either.
We’re in our mid 30s now and this happened eight years ago, after we’d both gone through rough breakups and a long stretch of moping and drinking. We were supposed to go out with friends and I let her into my apartment before I jumped in the shower.
I came out of the bathroom to find Madi kneeling on her hands and knees on my bed, naked, looking back over her shoulder at me. “Just don’t think.”
She knew me well enough to assume I was doing mental math on the wisdom of having sex again – but honestly, I was just more entranced by her pussy and ass. She had puffy labia (at one point I called them voluptuous – “did you just call my pussy fat?!”) that were framed wonderfully between her legs and I distinctly remember thinking about how light her butthole is and how nice her ass is overall – she’s curvy but fit, she was a dancer until she realized her body type (short, big boobs, big butt) worked against her. Perhaps my favorite thing, she had a bikini bottom tanline – not sharp relief, just a noticeable transition between tan skin and pale. Tan lines are hot.
While I was still entranced, she rolled over and sat reclined against my pillows and headboard, spreading her legs to give me another angle on her bare pussy. My ex had a full bush – which is also hot, in a different way, really it all works on the right girl at the right moment – and I was compelled to bury my face between Madi’s legs before we even kissed.
I have some self control, though, and I knew her feet set her off (we’ve discussed a lot over the years – the only kink of hers I wasn’t so sure about was choking) so I climbed on the bed and started at her toes, sucking them individually and massaging her feet. Once she was writhing sufficiently, I kissed my way up her legs until I was between her thighs, she was vocal, guided me toward what worked for her (fingers or tongue, not both – sucking gently, broad tongue not tip) and started repeating ‘yes’ when I pressed on her lower abdomen with my hand wrapped under her leg, starting to thrust against my face. “Oh yeah that was yeah needed that” as she pulled me up by the hair.
My beard was soaked, we started kissing – “I feel like I’m having my first girl-girl experience again.” “I hope she didn’t have a beard.” “This is better when we aren’t about to blackout.” “Shocking.”
Then I’m on my back and she’s working her way down, stopping to bite my nipples (unfortunately, not an erogenous zone – just ticklish) and grins as she takes hold of my erection. She gets me slick and strokes while she sucks and licks my balls, finally takes me in her mouth and begins to dip her head, inch by inch working lower until she can’t take more. “Fuck your mouth is amazing,” a pleased groan, hand around the base to keep me from thrusting too much, Madi starts bobbing in rhythm to my hips. I fill my hands with her hair, not to push but just wanting more physical connection.
I know I’m getting close and start to pull her off my dick. “I want to fuck you.” “Later, there’s time.” Back to bobbing, mouth off, stroking. “Cum for me, I want you to cum for me.” Now I’m thrusting against her and I feel the tightening and fill her mouth. A couple more strokes and she gently sucks on my head until I can’t take it.
We cuddle for a long time, kissing every and now then until I get up and make us a drink. “Sorry I surprised you, I just wanted to see your face when you came out of the shower.”
Her leg thrown over me, head on my shoulder, until I twitch against her and the quiet contemplation is over, I’m fully hard again as soon as her lips touch my dick. Madi straddles me and begins to slide down my cock, inch by inch until she settles in it’s been a long time since I’ve had sex without a condom and the sensations are overwhelming.
She’s bouncing, setting her own pace, until I take her hips and begin thrusting up, making her shout, Madi leans over so I can take her nipples between my teeth while she grinds against my pubic bone willing herself to an orgasm. She gets off and starts to suck me, tasting herself on my dick.
I position her for reverse cowgirl – “You just want to check out my ass some more.” “Shut up and fuck me.” – she starts to push back and I spank her right cheek. “Mmmmm. I don’t break.” I start to spank her harder, leaving a red print across the tan-line border.
No fear of cumming too soon on my end and fully over the “this is my oldest friend” baggage, we’re pushing each other harder and faster, from here everything starts to become a blur of bodies and squeaks and spanks and my mouth full of her nipples again. Moving to missionary we end up in my favorite position, sitting on the edge of the bed, her legs around my waist, arms around my neck, making out while I’m inside her, our hips shuffling (but does it really count as thrusting)? She bit my neck so I flipped her on her back, thrusting standing up with her toes in my mouth again but I really want to see her again and just say “behind.”
She kneels, poking her butt in the air with a wiggle. “Oooh” as I started spanking her again. I paused half in to enjoy the sight, her torso dipping down making her butt look even rounder, before I begin to thrust, punctuating with spanks, finding the right pace and strength when she starts saying ‘yes’ under her breath repeatedly. “Pull my hair,” I take her dark bob by the root and increase the pressure steadily until she moans.
“Do you want me to cum inside you?” Head nod. “Tell me.” “Cum in me, I want to feel it.” I’m pulling her hips back into hard, meeting in the middle, eliciting a series of “fuck fuck fuck fucks” until I can’t stop and cum with a last deep thrust.
We cuddled for a second but it was too hot so I ran and cranked the AC down so we could spoon in comfort. “We should probably tell them we’re not making it out tonight.” “I did while you were showering.”
We spooned and talked for a while before pulling up the comforter and falling asleep, we woke up early for slow, sleepy morning sex and both went off to our days. And… that’s it, we never had sex again or came close, it broke the dam on our moping and whatever residual sexual tension lay between us.
I introduced her to a new co-worker, her now-husband, a couple of years later.
Source: reddit.com/r/gonewildstories/comments/rex991/fucking_my_oldest_friend_gets_us_out_of_a_funk_mf
Woah
Sad ending
Bittersweet ending but glad it worked for both of you.