my intro, my story, my disaster

My lack of success, a wholesome tale still yet to reach anything close to its conclusion. I'm a 29 year old male, pretty neat huh.. nope. The endless searching and failed attempts have me feeling like a hoarder. I will add quickly that I don't have expectations nor do I believe this is owed to me. Just thoughts to touchscreen while my bored ass sits up on night shift swiping the hours away on tinder looking at Tiffany, 25, very capable and not in need of a partner however could go with a dom to put her in her place, Jessica, 32, an all round life enthusiast on an endeavour to find a solid connection with a lad who isn't afraid of a challenge and then there's me, Sam, 29, blah blah blah. My journey started with an ex who wasn't an ex at the time but is now during the telling of this story an ex, still with me? Let's call her "M". Now, untill I'd met M my dating life and sexual experiences were vanilla at best, an aspiring chap with one hand on his heart and the other cradling his balls just trying his best. I'd just met M and things were going well, cupcake stage was in full effect and the sex was awesome. I was picking up new tricks, I had gotten better at old ones and then one warm, sensual night it happened. There we were, me on my back on the floor, M on top riding thrusting back and forth on me with one hand beside my head supporting her balance while the other hand made its way back below her rear, fondling my testicles like a couple of those metal balls with the bells in them that you spin in your palm, the purpose of those metal balls I'm still not sure of but the point here is that during said fondling, M thought she'd be a little adventurous and went a bit further. My train of thought jumps straight to her hand placement and intentions. Feeling a slight panic, i shake the thought and go back to grabbing her hips. pushing and pulling with the motion of her thrusts, I begin to tense up a bit, "she's still going further.." I think when all of a sudden she connects with my spot and within seconds of her fingers touching and rubbing my anus I shot off like a rocket. A warmth had come over me i hadn't felt before. For me it was a new and rather enjoyably uncomfortable sensation, nothing new for M. This had me in a deep thought shortly after, asking myself "do I ask for that again? Is this a play I like?". The idea of even starting that conversation was uncomfortable enough, being a typical egotistical male at the time, I couldn't shake the thought of me enjoying such a thing. I thought I'd leave it, just brush it off for the time being. Well at least I tried to, the very next day we were back at it again and sure enough, back goes her hand and without a moment of hesitation I felt the tips of her fingers and nails hit the spot. Rubbing, round and round, faster and faster, I find myself drowning, mentally grasping a firm hold of reality mixed with ecstasy. The same feelings and thoughts come rushing straight back to my brain but before I knew it I was edging a climax. Fighting back the urge to stop, I release myself, filling her tight, warm pussy as she applies even more pressure to my hole. Heavy breath masking my "oh fuck oh fuck", I finally reach the end of an intense orgasm and pull her back onto me. Lying there feeling her weight on me as we melt together in that sweet moment of bliss i turn and bring my lips to her ear and whisper, "I didn't know what to think about that yesterday but I'm glad you did it again, hard to explain exactly but wow, I've never had anyone do that, never thought to ask". M was great, the way she explained her history, teaching me that there are more people than I'd expect who loose themselves to this kind of play. Instant relief, I'm not alone, cool beans.
A new eara of play?