Three Times – a Charm!

I invited a guy over around midnight for a pump and dump, since he preferred being the first load in a hole, and he was actually a lot cuter than his pictures, which is always a bonus. He told me while I was sucking his dick that he never came from blowjobs but he was sure he could with me sucking him off. I asked if he wanted me to get him close orally and then sit on it right before he shot, but  he said he really wanted to fuck me, so I rode him for a bit and then he asked me to bend over and he fucked every last inch of his dick into my hole and had the hottest orgasm where I could tell it was taking every effort to keep quiet so my roommates wouldn’t hear.

I had talked to another guy before inviting the first one over and tentatively planned to meet up after he finished some errands. To my surprise, he arrived not five minutes after the first guy shot his load into me, and I went to meet him and we went to the backyard because I’m not comfortable enough at the place I’m subletting to take the revolving door approach I usually would in my own place in such a situation. He fingered my hole as I had a cigarette and commented on how wet it was, and he tasted his fingers a few times, but he didn’t say much and was the kind of non-emotive men that I tend to worry about whether they’re into it or not so I didn’t know what he was thinking. I made an excuse to try and get him into the gated parking lot next to the loft which I felt would be a safer place for him to stick appendages up my ass, and finally got us back there behind the loft that borders the lot. I was really worried because he looked annoyed but then I noticed he’d taken out his dick and it was both hard and very nice, and after some awkward positioning I finally swallowed all of my very palpable nerves and fears and bent over against a chair and he slid inside me and fucked me from behind for almost five minutes without stopping, and with each passing minute I was becoming more and more overwhelmed until a weird thing happened. It was almost like I grew so overwhelmed and scared and excited and worried that suddenly I just thought “fuck it,” and I looked back at him instead of looking around and keeping watch. And literally the moment I made eye contact with him and he saw in my expression that I was all in, he shot his load in me, and it was one of the hottest moments of my entire sexual career.

The problem was, I’d ripped the shorts I had on all the way up the back as he fucked me through them, and there were two guys sitting in a car they’d just jump-started right outside the gate of the parking lot, and I couldn’t get to my place without them seeing it all. So I waited in the lot for twenty fucking minutes and the assholes didn’t move, and finally I came to my senses and reminded myself that I would never see them again and it was more important that I get back home than that I avoid embarassment that really wasn’t that big a deal to begin with. So I held my shorts closed and walked out and down the sidewalk to my apartment, not looking at the car and trying not to think about how they must have reacted, and half a minute later I was back in my room with two loads in me.

Within half an hour I’d hit up a 26 year old Latin guy who said he wanted to breed me and was excited that I had cum in me already, which is basically the hottest kind of guy to me, and as I texted him my address my phone informed me that it was a guy I’d met through a friend months earlier who had pursued me on numerous occasions but I’d never met up with because I erroneously thought he had told me he didn’t bareback, which was a shame because I wanted to play with him. So both of us were really excited to finally meet up, and he really lived up to what he said he liked, and we had major sexual chemistry and got along really well. He shot a load in me standing up within the first ten minutes, then over the next four or five hours we got to know each other generally and found we also had a lot in common in other ways, and I especially liked that he really got everything I was talking about in terms of my writing, my mentality, my personality, etc. Frankly it was a lot like the early days with my ex boyfriend, with the one key difference being (and this is in no way a criticism or a bad thing at all) that my attraction to this guy was and is a very different kind than my attraction to my ex, much more in a friend/sex partner way where the ex was more of a brotherly/care-taking/puppy love attraction.

He finally decided to head home around 7am but not  before fucking me one last time, and he fucked me on my back with my legs up and his cock was big enough and he fucked deep enough to become a member of the exclusive club of guys who’ve made me cum without touching my dick just by fucking me. As I began to feel myself getting close I grabbed my dick and pulled it down toward my hole so the head rubbed up against his dick as he fucked me, which led to a few moments where his cock thrusting into me pulled a bit of my cock head in with it, not in any absolute way but enough that both of us had this awareness that he and I were  double fucking my own ass in a way, and finally I had to cum and it was quite intense and went everywhere, and I lay there pretty much paralyzed as he shot his load on my chest and my hole. I was completely transported as I lay there and I kept saying that the whole liaison had been perfect, start tov finish, which it kind of was and what a fucking perfect time for me to experience a perfect hookup, right? Everything about my time with this guy was as successful as most of my sexual experiences for the last several months have been failures. Not only was almost everything about last night fun in the moment, the fact that I had so much success last night basically validates everything I’d set out to try and do. Maybe it was fate, maybe it was me doing things right finally, maybe it’s coincience, I don’t really care… as far as I’m seeing it, I’m trying out a new sexual strategy and initial signs are all suggesting I’m on the right path.

Plus, check out this amazing and completely un-retouched shot the last guy took of me…on my iPhone no less!