Since my last story seemed popular, I thought I’d share another story from around that time. This story occurred about 2 months prior to my previous story. It was the night before I moved across the country for grad school, and the conclusion of an interesting summer involving two girls. I’ll give a little background information on each, and then get right to the story of the final night. This is definitely one of my sluttier confessions. It’s going to be a long story.
Early in the summer, I connected with a girl on Twitter, who we will call Jessica. A couple of likes and retweets laters, she sent me a DM, and after a day or two, we had exchanged numbers. Jessica was short, had blonde hair, and had a nice, soft body with big breasts. We hung out a couple of times at some of the popular spots in our areas with our groups of friends. Not long after that, we began hooking up. What started as a movie night at her place that turned into a blowjob became a regular thing about 2-3 times per week. Because I lived with family, I would go to her place after work, we would fuck as soon as the door closed behind me, hang out and watch a movie, then fuck again before I left for the night. It was a great arrangement. What made it even better was that we got along with each other’s friends, so we didn’t have to sneak around in silence.
Then there was Hannah. Hannah was the exact opposite of Jessica. Dark hair, tattoos, fit body, small breasts, but a real big ass. I had known of Hannah for years through social media and mutual friends, but never really interacted with her. One night, I liked a couple of her Instagram pictures, she liked a couple of mine back, so of course I sent her a DM. We exchanged numbers, and I ended up seeing her out a week or so later. The thing is, she had a boyfriend (that she didn’t really tell me about for a while), so I didn’t make any advances. We hung out in a group throughout the summer, often using my house as the pre-game spot before heading out. There was one night she left her car and took an Uber home from the bar, and had to come pick it up the next day. She came inside and hung out for a little bit, and we started to get close, but she left before anything happened. I won’t deny that I wanted her BAD, but I respected her boundaries. The way she always flirted with me drove me crazy. She texted me a picture of her ass in a thong one night. She then messaged me that she was so sorry and meant to send it to her boyfriend, but she made it so clear that she wanted me to see it. The only thing I could think about was fucking her at this point.
Fast forward to the end of the summer, and it’s my last night in town. I was out at a popular bar saying goodbye to a lot of my friends. I told both Jessica and Hannah I would be there. My friends new about Jessica and I, so she was around us frequently throughout the night. She was a little sad because I told her that our summer fling had to end. The truth is, I didn’t want to move across the country trying to maintain a long distance relationship with someone I had just met a few months prior. She was completely understanding and handled it really well. Hannah knew it was my last night in town as well. While she didn’t come around me as often, we did talk a couple of times throughout the night.
At the end of the night, it was time to go home. I said goodbye to Hannah and gave her a hug. Then I went and found Jessica. Jessica handed me a letter and told me to read it in the car. It was a goodbye letter, telling me how much fun she had this summer and how glad she was that we met. She texted me while I was on my way home to see if I wanted to come over to see her for one last night together. Just as I was about to respond, I received another text; this one from Hannah. It said that she was coming over to my place. After everything Jessica had done for me that summer, and after reading that nice note, I texted her back and told her I was sorry but I couldn’t. One more night would have made me too sad. She said she understood, and that we should keep in touch. Then I texted back Hannah and told her I’d see her soon.
Given our history, I really didn’t expect for Hannah to show up that night. And I wouldn’t have blamed her for not showing up either. But sure enough, 45 minutes later (3:00am at this point), she texted me that she was outside. When I let her in, we went straight to my room. Since we had never really discussed sex before, I didn’t really know what to expect. I didn’t even know if we would be having sex for that matter! For all I knew, we could have just been talking and saying goodbye.
As soon as the bedroom door shut, Hannah took control. She pushed me onto my bed and undid my belt and zipper and pulled my pants and boxer briefs down. In the same motion, she dropped to her knees and began sucking me off. It started slow and tender, but got fast and sloppy not soon after. Her being a freak was the best surprise ever. She kept trying to take it all in her mouth, before gagging and pulling it out. She was SO into it, which made it even hotter.
I stood her up, and she stripped all of her clothes off for me. Her tattoos and toned body were amazing. I laid her on her back on the bed and spread her legs open. She had the most perfect innie pussy I had ever seen. I teased her for about a minute by rubbing the head of my cock on her clit and rubbing through her slit, before I put the tip in. She was TIGHT. She wrapped her arms around my neck, and pulled me down to her, pulling my cock deeper and deeper. It took about a minute of thrusting before I was able to get all the way in, her moaning in my ear the entire time. I couldn’t believe it was actually happening; it was what I spent a summer fantasizing about, and now it was coming true.
She said let’s switch positions, so I pulled out to see what she would do. She got on her hands and knees on the floor, face on the carpet with her big ass up in the air. She said “fuck me from behind”, so I got down on my knees behind her and slid back into her tight, wet pussy. At first I went slow, but started picking up the speed a little bit more and more. Her moans got louder the faster we went. I asked her if she liked that, and she yelled “harder!” so I grabbed her hips tight and started thrusting as fast as I could, the sounds of our skin smacking echoing. I had tried to keep us quiet as I was staying with my parents for the summer, but at this point I didn’t care, as they were two floors up and I was never going to have this opportunity again.
After some rough doggy, she wanted to get on top. She put me back on the bed seated up against the headboard while she climbed on top, facing me. The first time we ever kissed was in this position, which I didn’t realize until after we were done. She found the perfect rhythm and pace, and continued to moan into my ear. This was better than I could have ever imagined. My hands gripping her ass, her hands exploring my body.
Without warning, she got off me and pulled the condom off, and immediately started sucking. At that moment, I wasn’t really close to finishing, but after a minute of her sucking, I felt ready to cum. The orgasm was one of the best I had ever experienced. She did not miss a beat, and kept sucking up and down as I was shooting cum down her throat. My entire body was shaking as she slowly pulled my cock back out of her mouth, sucking off every last drip while looking up at me.
It was extremely late at this point, and she said she had to go. Her Uber arrived, and I walked her outside. As soon as I got back inside, my head hit the pillow and I passed out. When I woke up, I thought it was all a dream. Luckily, the condom wrapper on the floor by the bed was a reminder that my dream did come true, and it exceeded my expectations.
I moved across the country the next day, and everyone moved on with their lives. But that was a summer that I will never forget.
Source: reddit.com/r/gonewildstories/comments/gtjf49/m_i_didnt_let_her_be_the_one_that_got_away