Red Wings

So by June of 2012, I had become quite a frequent user of the Craiglist personals section in the Chicago area. I'd had a few encounters, most satisfactory, others not so much. But today I was on my period and contemplating my next move. I knew I wanted to cum and that pleasuring myself just wasn't going to do it for me. So I placed an ad stating my current predicament, and then sat back and waited. It took a surprisingly short amount of time to elicit responses. I suppose some were just desperate, some didn't care and a few were fetishists. I chose someone who I thought fit the middle category, and made arrangements to go over.

After a 20-minute drive, I arrived. Harry came downstairs to greet me and we went back up. He was pleasant enough looking, late 30's, Mr. Clean bald and in good shape. We went upstairs and chatted for a while. I don't remember too much about his place, other than he had a really awesome cat.

We made our way into the bedroom and he undressed me slowly and sensually. I'm always particularly nervous with bigger men, even though they're my physical preference. It adds an element of danger that I suppose I've grown to crave. After he had me naked, he just looked at me for a while. I'm not the most self-conscious person in the world, but it was a little unnerving. Then he laid me down and crawled on top. We kissed like two high schoolers who were stealing a moment away from watchful eyes. Deeply, passionately, like nothing else in the world mattered. His hands massaged my tits, softer than I was used to, but it felt so good. He worked his way downward, kissing my ears, my neck, and the spot between my breasts. Then he decided to focus his attention on them. He suckled me like a newborn, alternating his pressure and intensity. By now, I was moaning quite enthusiastically.

After spending what seemed like forever worshipping my soft, full tits, Harry continued downwards. He kissed my belly, he sucked on the ultra-sensitive spots right by my pelvis, which caused me to squirm and moan. I wanted him to keep going, but I knew I couldn't ask. I'd only just met the man, I was in no position to ask him to stick his tongue in my scarlet cunt, no matter how wet and achy it was. He must have been reading my mind, as his tongue dipped lower and lower. First it found my clit. The slightest touch made me quiver. I've been with enough women to know that I'm more response than many of them and he was reading all my reactions and acting accordingly. He sucked my clit, flicked it with my tongue until I knew I was going to explode. Then he did the cruelest thing possible, he stopped, and to my surprise, he went lower. He started licking me from asshole to clit, all along my slit, which was wet with more than one fluid. It felt too good for me to care or be ashamed. I put my hands on the back of his head and guided him, I begged him to tongue-fuck my cunt, which he did. I felt my body just completely open up and release to him. I came in an incredibly intense moment. I think just the taboo of the whole act excited me as much as anything else. By the time we'd finished and I looked at him, his face was a mess, I felt the slightest twinge of guilt and apologized. He just smiled and told me to worry.

After a brief cleanup session, Harry led me back to the bed and put me on all fours. I don't know it is about this position that I love so much. Maybe its just that I sleep with so many men who I've no interest in and in this position, I don't have to make eye contact. Maybe it's just that this position achieves some of the deepest penetration possible. Maybe it's that my ass is exposed to either penetrate or spank. Most likely it's a combination of all of them.

He slid in behind me, his hard and quite impressive cock pressing against sweet crimson hole. He slid in without the slightest resistance, bottoming out against my cervix. He was thick too, and I felt so pleasantly stuffed. My cunt completely encircled his cock, squeezing it, feeling every inch. He started thrusting slowly at first, but something primal took over in me and I began begging for harder. I wanted that big cock to fuck me like a slut should be fucked. I was thrusting back against him as he thrust into me. Every stroke hurt a little as he pounded against the depths of my being. But I didn't care; the reward was just too good. He slapped my ass a time or two. It just wouldn't be a proper fucking without a little spanking. I reached back and spread my ass apart for him so he could watch his cock going all the way in and out of me. As worked up as we both were, it didn't take me long to cum. And then cum again, and again; eventually I just lost track. One of those tight contractions proved to be too much for him and he spilled into me. My cunt was a delightful mix of bodily fluids, both mine and his and he bent down to taste. He offered me a kiss after, but that was just a little too much for me.

We had a quick shower and then lay back down. I ended up spending the night there, which was very rare for me, but I was tired and I trusted him not to stab me in my sleep. After I left the next morning, we promised to stay in touch, but these things never work out and so I'm left with nothing but very fond memories of a man who went where no man had gone before.