Ok, so this is a story about the first time I had real anal. (I had tried with someone before, but he was much to large for a first time). So at the time, I must have been 18, and being very promiscuous. Back when craigslist still had personals ads, I was very familiar with them. It wasn’t the first time I had posted an ad looking for my next victim, I mean, sex partner, and wouldn’t be my last. The first few responses were very dull and not really what I wanted this particular night. Then a local guy popped up, and either he looked extra enticing, or I was just fed up with the scrolling of emails, he was it. He drove to pick me up, and we took a short drive to a long driveway in the woods. I lived in a very rual area, so most of the roads and driveways were dirt and gravel. I’m not sure if it’s just me, but sex with a stranger always seems to start out awkward. Do you undo his pants, should you undress first, but you get into the swing of it, and everything moves pretty quick. After a few minutes of touching and kissing, groping and sucking, I end up in his lap on the driver’s side. As expected, it didn’t go very well. My ass is too large to be bumping around in the driver’s seat, it kept getting stuck under the steering wheel no matter how we adjusted things. Frustrated, both sexually and with the situation, we got out of the car, and decided another tactict might work. I was use to being bent over things, or holding my ankles, I was quite flexible, so it should be a piece of cake. As I lay over the hood of his car, panties still around my ankles, I waited for him slide in. He had a few inches in height on me, and he kept thrusting a bit high. I kept trying to reposition him, thinking I my tip toes might help as well. Then he’s says to stop, he knows what he’s doing, and trust him, I’ll like it. Between the lines on the condom and how wet I already was, he slid his cock into my ass, and it was a rush of pain a pleasure, confusion of do I like this? All the while he is pumping harder and harder and a feeling of extacy is building and building, and before long, the confusion is gone, and I’m in love with it. My arms went weak, my torso just rocking on the good with each thrust. All I can do is lay there and wait to regain control of my limbs. He finishes and we both readjust for the drive home. It’s not far for either of us, which is nice after an unexpected orgasm.
In my drive, he parks and opens my door. We exchange our pleasantries to go, and he has one last request. He asks if he can give a facial. I’ve never had anyone cum on my face before, and why not give it a shot. Right there in my driveway, I got on my knees, and he undid his zipper. It surprised me how little work I had to do, he wanted to be in charge I suppose. So I knelt patiently until he began to erupt, and with each spasm, more and more splashed onto me, my face, my hair, and down my chest. With that, we parted ways, and I went on with my night.