Long one: in my mid to early twenties I had a very close friend and we used to coyly flirt but never did anything. Only after this experience did I find out she always wanted to fuck but I didn't know, and was too shy to ever act on it.

One day with her about her about to break up with her bf with and me having just broken up with my gf we were having our catchup. Both our situations being frustrating we were helping each other through - my friend went from having her hand on my knee in sympathy to sliding up and down, and just touching the tip of my cock. I closed my legs instinctively and we kept chatting. Looking for reassurance of her view at one point, she ended up with her hand back on my thigh, higher up, squeezing my leg but her fingertips were grazing my cock a lot more deliberately now. I was obviously getting very horny but was uncomfortable going further and (being a sheltered ignorant fool) was unsure as to whether or not I was misreading things. She must have been able to tell because we wrapped up for her to head home. Then out on the street by her car we had a big hug and she clearly felt my throbbing cock against her body. She kissed my neck lightly, I kissed her ear, and we ended up making out under the shadow of a tree, slightly sheltered from the bright streetlight, on the bonnet of her car.

Before long my cock was in the firm grip of her hand, and my fingers were sliding up and down the wonderfully warm wet of her lips. Then she was jerking me off on her clit. I ended up blowing on her pussy, and with some backed up reserves a lot of cum exploded on her and filled in the gusset of her panties. Moments later I felt her body convulse as she came on me, both still stood out on the street! I put my cock away shyly, she did her jeans back up (with my cum still in there) and we just burst out laughing. We were both so shocked, we just awkwardly kissed, said goodnight and she left.

We didn't speak about it for a few days, then started sexting each other but agreed nothing was going to happen until the breakup was done. A week after that she came over, upset because she had tried to end it but he was refusing to accept they were through. After a serious beginning to conversations we started with giggling at what happened the previous week.

She put her hand on my crotch and said she couldn't believe she had "this" on her clit, and I slid my hand up her skirt to her panties, nervously laughing at having blown my load in "here". Before long we were making out like crazed teenagers and tearing each others clothes off. I pinned her down on the couch and slid my cock up and down her pussy making both of us quiver with every pass of my head on her clit. After a minute or two of us both gasping and shuddering in pleasure I pushed myself inside and we were both fucking each other with this desperate, intense, desire. Started there in the living room on the couch, then somehow moved to kitchen bench, then on the laundry floor, and finished off lying on the grass in the back garden, in the dim light of the moon. Laughing about how unbelievable it was that we finally did that, some minutes later in the brighter moonlight I saw that the neighbour's (university aged) daughter was peering out her window at us! Normally I'd have been mortified but I suddenly had no such feeling (and I now enjoy a bit of exhibitionism). I have no idea when she started looking and how much she saw. Hope you enjoyed the show if somehow you're reading this today!)

The whole experience was incredibly hot and still turns me on to think of it, but is tinged with the guilt of having had sex with her while someone else still felt she was his girlfriend. We ended up fwb for a while and then went separate ways because (as is inevitable) it couldn't last without repercussions on the friendship (cue Seinfeld & Elaine "this that and the other" conversation).