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I was sitting at the bar, waiting for a friend, when the first guy (Mark) approached me. He was around my age, taller than me, good-looking. He asked if he could get me a drink, and since my friend was running late, I accepted. We chatted for a while, and he was charming enough for me to decide that if my friend didn't show up soon, Mark would take me home.
Then Mark got a call, and he excused himself to take the call outside the bar. At that time, I got a text from my friend apologising for having to bail out on me. I was more than happy to accept her apology.
Then, the second guy approached me. He (Jim) said he had just seen my previous companion leave me and was wondering what was wrong with that guy. I laughed and told him he was just on the phone and he would be back. Jim light-heartedly cursed his luck and asked if at least he could buy me one drink. Since I was running a little dry, I accepted. We chatted for a while, and then Jim left me with my drink.
Since Mark was taking a long time to come back, I checked with the bartender to make sure everything was paid up and stepped outside to see if I could find him. He wasn't outside the bar. I looked around the street, but he was nowhere to be seen.
I think Jim saw me walking up and down outside the bar, and he came out to see what was going on. I told him that my potential date seemed to have disappeared. He commiserated with me, and just a few minutes later, we were walking arm in arm through a nearby park.
Jim pointed out that the park had a small hill, and the view from the benches there was great. I didn't find out if that was true because once we got to the bench, I was sitting on his lap, kissing him. Jim had one hand on my ass and the other on my right breast. I could feel him hardening under me, and I broke the kiss and slipped off his lap. Kneeling on the wet grass, I undid his pants and got his cock in my mouth. Jim held my head, sometimes pushing as I sucked him into my mouth all the way down. I reached down and pushed my panties aside to play with myself as I sucked him.
After sucking his cock for several minutes, I wanted to be fucked. So I stood up, intending to ride him. But Jim stopped me. He told me he didn't have a condom. I told him that was fine, as I was on birth control. Jim said the last time someone told him that, nine months later, he was a dad.
That kind of took the wind out of my sails. First, a guy disappeared on me, and then I found the only guy in the vicinity who had qualms about having sex. Right then, I desperately wanted to get fucked, so without thinking much about it, I asked in that case if he would be willing to fuck my ass.
Jim was willing. Within seconds, I was kneeling on the bench, my dress up around my waist, panties torn off, and flung into the bushes. Jim was standing behind me, one hand spreading my ass as he guided his cock into my ass. My spit on his cock was the only lube we had, but I was more than happy to suffer a little pain to be fucked. I again reached down and started playing with my clit as Jim worked his cock in. He wasn't overly thick, but he had to push hard to get his cock all the way into my ass.
Whenever I let out a moan or cry of pain, Jim would stop and ask if I was okay. I got tired of that and told him to shut up and just fuck me. He finally complied. Jim grabbed my hips and started fucking me. It hurt, but it also felt good. Between that and my fingers on my clit, I had my first orgasm in minutes. Jim felt my orgasm, and it drove him wild. His grip tightened, and he started pounding me. He didn't last long, and within moments, his cum was filling my ass. That sensation always elicited a primal feeling in me, and before he was done, I had my second orgasm.
When he was done cumming, he pulled out of my ass. I could feel his cum drip out of me. I collapsed on the bench, curling up. I kept playing with my clit, enjoying the sensations.
When I finally looked up, Jim was gone. I didn't even hear him leave. I was a little pissed that he had just left me like that, even without a thank you. I gathered my belongings - those I could find; I had no idea where my panties were, and I didn't fancy crawling into a bush to look for them. I cleaned myself up as best I could in the dark and walked towards the park entrance. I could feel Jim's cum dripping down my thighs. My dress was knee-length, and I thought of finding a restroom to clean up properly.
But just as I turned the first corner, right in front of me was Mark. We both stopped and looked at each other. He spoke first and asked where I had disappeared to and then gave me a quick once-over and asked if I was alright. I told him I was fine, and I left because he had disappeared first. He got an embarrassed look on his face and said he had to get something. I asked him what was so important. He looked even more embarrassed and said it didn't matter. I pressed him more, and he told me he went to buy condoms. Given my situation, that was funny to me, and I started laughing. Mark asked me what was so funny. Since I figured Mark would skedaddle out of there once he knew, I told him bluntly that after he had left, a guy approached me, and I just let him fuck my ass bare.
Mark's response was simply, "That's hot." I think I did a perfect impression of the surprised Pikachu meme.
Mark walked up to me, told me to show him and put his hand around my waist, spinning me around. Then, right there, on the open street, he lifted my dress. His fingers pushed into my ass, and I just let him. He said nothing but took me by the waist and led me back into the park. He bent me against a tree and, without a pause, he had his cock out and in my ass. Mark had an easier time getting in than Jim. And he also lasted longer. He held me against the tree and fucked my ass relentlessly. I was pressed tightly against the tree and couldn't reach down to play with my clit, but I still cummed twice more before Mark filled my ass.
Mark was better than Jim. He helped me clean up, and then we exchanged numbers, and he called me a cab. We did meet up a few more times. I never saw Jim again.
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