Many years ago I worked at a job in the entertainment industry that required me to wear a suit. That and the somewhat authoritative role I played was not unhelpful when it came to flirting with coworkers and even the occasional patron. This story is regarding the latter, a slightly older woman (at the time I was in my early twenties and she was young looking but in her early thirties, an actual MILF). She was relatively tall (I'm 6' and she was a bit shorter) and very slender, with alabaster skin, copious freckles, and dark auburn hair a bit past her shoulders. She was a regular, and was in the habit of coming in when I was on shift and wearing a low cut blouse that showed off what little cleavage her petite perky breasts could manage, and, most importantly, the tiny gold crucifix she wore between them. For some reason that cross set off the whole package for me.

She would always give me the doe eyes, so I had the feeling she was attracted to me, but I knew she was married so I never made any kind of move. My coworkers and I tended to party hard. After our shifts were over, we'd often meet for shots or what not. Frequently this would be after the bars were closed. It also wouldn't be uncommon to see regulars fraternizing with employees outside of work. I lived in a house with a couple of roomates who worked with me. So maybe it was inevitable that one night after a long stressful shift, I found myself at home, still in my shirt and tie from work, drinking with coworkers, when a couple more coworkers showed up with her in tow. As soon as she walked in she gave me a look that made my balls tingle. She was wearing a black dress, not super short, but simple and snug, showing off her lithe body. We started chatting and she coyly informed me that her and her and her husband were recently separated. My first reaction was one of consolation, but I doubt I masked my excitment well. At this point, my slightly intoxicated mind lost all moral qualms with flirting. For the remainder of the night I was laser focussed on her and she was on me as well. The rest of the party faded away as we chatted about nonsense, our minds elswhere. Our eyes locked, she was playing with her hair, I couldn't stop glancing at her lips and licking mine. I made up some excuse to come to my room. I lived in a mother in law unit behind the house, so it was quiet and private. I made some tea and put on some music and we sat on my couch and chatted some more. She was looking me up and down like I was her next meal and the excitment was going straight to my cock, making the bulge difficult to hide. I can't say for certain if she noticed, but her interest somehow increased. It seemed like the tension was getting about as strained as it could be so I made the first move. I put my hand on the side of her face and pulled her in for a long kiss. We stayed there for what seemed like ages and an instant, exploring each others' sensitive lips with our tongues and teeth. Our hands started roaming over each other's bodies, first caressing, then grabbing and pulling. I ran my fingers up her thigh under her dress and massaged her clit through her black panties.

Her moans stopped abruptly with a little grunt of frustration and she got up and stalked over to my bed, slyly smiling and beckoning me to follow. I was uncomfortably hard and it was clearly showing through my slacks, a thick bar running down one leg. She got on my bed, on her hands and knees, facing me. I walked up to the edge of the bed, taking off my tie quickly and unbuttoning my shirt. She went straight for my fly. She unzipped and pulled out my now diamond hard member and said in a breathy voice "oh foxtrotalphapapa, EVERY part of you is amazing". Now most women I've been with don't really know what to do with a long uncut, thick cock, let alone one at peak arousal. She was an exception. She crawled forward and her hot mouth enveloped the first few inches of my dick as her hands wrapped around the shaft. While she wasn't trying to deep throat it, she had me reeling in seconds. I stroked her hair in encouragement and told her she was doing an amazing job. The image of this woman I had fantasized about on her knees sucking my hard cock was nearly enough to send me over the edge. She must have noticed, because she quickly repositioned herself on the bed so she was lying on her back, legs spread, grinning ear to ear. She was offering herself to me, but I wanted to check how wet she was before diving in, so I put one knee on the bed, bent over, grabbed her behind the neck and kissed her deep. Then I reached down, and moving her panties to the side, played with her clit a little before spreading her lips and pressing on her opening lightly. Not wet enough, I concluded, so I got down on the floor, grabbed her hips, and firmly pulled her to the edge of the bed, hiking her dress up over her cute little ass in the process. She let out a little yelp and giggle in surprise at this, which really got me smiling. I firmly grasped her panties with both hands and slid them all the way off.

I kissed her inner thighs, working my way down to my snack. I started by giving her one long, slow, gentle lick, then worked on her clit, gently at first, but gradually increasing in pressure and speed. From her moans and squirming, it seemed like she was enjoying this, so I took one hand off her hip and pressed my long middle finger, palm up, inside her, never letting up on licking her clit. Her little gasp shot a thrill through me as I started to stroke her A and G spot with a come hither motion. She was definitly soaking wet now, but I was having too much fun to let her feel my throbbing cock yet. After awhile I inserted my ring finger as well and continued stroking her sopping cunt. Her moans were driving me crazy and my cock was driving me me to quit playing, so it was extremely fortunate that at that moment she let out a cry of ecstasy. I could feel her pussy pulsing on my fingers as she came for the first time. I let up on her clit after it seemed like she was done and gave her some gentle, full mouth kisses over her whole vulva, causing her to giggle and convulse with sensitivity.

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This is my first attempt at writing something like this and it's getting kind of long so I think I'll break it up into two parts. Let me know if you like it and any constructive criticism you might have on the storytelling.

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Note:

This is the first story in a series of stories that are meant to be cathartic for me and hopefully enjoyable for you. Throughout my life I have been insecure sexually to varying degrees despite having a big dick. As I look back, I realize I have many regrets: times I wish I would have been more assertive, less reserved, more confident, more dominant, etc. Each of these stories starts out completely true, although I may change some minor details to protect identities, or fill in things I've forgotten, obviously. Then at the point where my regret begins, they diverge into fantasy. They will be mostly true and embellishments will not have anything to do with my penis size or my patners' reactions to it, nor any other aspect of my or my partners' bodies for that matter. Feel free to guess where the divergence takes place or just enjoy the story. I hope I'm not breaking the 4th wall too much for the rules of the sub by admitting part of the story is false.