Here’s Part 1: [https://www.reddit.com/r/gonewildstories/comments/9ne6v1/amazing_sex_with_my_first_kiss_more_than_a_decade/](https://www.reddit.com/r/gonewildstories/comments/9ne6v1/amazing_sex_with_my_first_kiss_more_than_a_decade/)
This story takes place the next night. For those who don’t want to read part one, here’s the summary: I was in NYC for a business trip, hit up old friend Tina who I knew in high school and happened to be my first kiss. We’re both now 27. We got drinks, went back to her place, and had amazing sex.
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After a day full of jam-packed meetings, as is usually the case on business trips, I got to Tina’s around 8pm. I had only one night left in town and after the night before, I couldn’t wait to make the best of it. I knocked on Tina’s apartment door and she answered wearing only an over-sized tee shirt adorned with our high school’s logo. We didn’t even say a word, she just jumped into my arms and we began making out, her pussy already wet, transferring moisture to the area of my shirt right about my belt as she straddled me.
She led me right to her bed, slipped the shirt off over her head, and told me to fuck her hard. I stripped as quick as I could and went to town, fucking her extremely hard in the missionary position, eventually putting my hands under her but and lifting her lower body in the air. Her pussy was freshly shaved from last night, and the outline of her abs became present as I fucked her at this angle. Her perky boobs bounced up and down, and she grabbed them with her hands, moaning as her red hair swung over her face.
After a few minutes, I was sweaty and already getting close, and personally I didn’t want this to be a quickie. We had all night, and I always need a few hours to recover. I slowed down the pace a little bit, fucking her hard but with extended pauses between each thrust. This drove her mad. I could tell she was on the edge of an orgasm.
“I want you to fuck my ass,” she said, the first words we had spoken to each other since I arrived about ten minutes ago.
I was in shock. I had never done anal, and I really didn’t know that people casually did anal. I certainly wasn’t opposed, just in awe.
“Okay,” I said, the only response I could think of.
She got up, went to her bedside table, and grabbed a bottle of lube and a condom.
“Lube my asshole up good, don’t be afraid to stick a finger inside,” she said, and positioned herself in all fours, her tight asshole right in my view. I did as instructed, and I found something about it so sexy. Not only was this new and exciting, but she was so domineering and at the same time, so submissive. She had total power over me by giving me total power over her.
After a minute, my index finger was fully inside her ass, and began to rub down, back towards me, like I was petting with just one finger. She began to moan uncontrollably and finally demanded that I enter her with my dick. I went to and…I had gone soft.
This obviously happens sometimes, and it’s always from nerves. I was certainly nervous in this situation. Some girls react poorly, so I began to get nervous about that, but went she noticed she just laid me down, got on her knees against the edge of the bed, and began to suck me off.
“You ready to fuck my ass?” she said, as she stroked my hardening dick. My anxiety quelled, I felt myself returning to full strength.
“You have nothing to worry about,” she added. “You’re going to be amazing. I’ll even put the condom on your dick for you right now.”
I always love when girls put the condom on after foreplay, and at this point, I was harder than I had been. I was the level of hard when you almost feel like you’re dick is going to pop off. It felt incredible as she rolled the latex down my shaft. She got back into her doggie position, her ass up. She spread her cheeks, and her asshole was still plenty lubed up from my handiwork before.
I positioned my dick against her asshole, and slowly entered. At first it felt impossible, then it felt weird, and finally, as I was almost all the way in, it felt unreal. I had never felt a sensation that was so tight, so stimulating, and yet, so smooth. I reached my hand around and rubbed her clit as I thrusted into her ass. Unlike porn and some stories on here, I wasn’t “pounding” her ass like a machine. I was fucking her slowly and rhythmically, and she was lost in some other dimension. Her head was buried to deep in the mattress that I couldn’t even hear her scream.
I blew my load without even realizing I was about to. I was so lost in the sensation and the euphoria of the moment. She clearly felt the warmth filling the condom, and breathed heavy as I climaxed. I rolled over next to her spent, and just lay there in awe. What a trip this had been.
She ordered in some Chinese food and we put The Office on Netflix. I didn’t know if I was going to stay over, but I was certainly hungry. She went and showered and came back in her robe, laying down on the bed next me and giving me a high five.
“Nice job bro. Really glad you came her on business,” she said, so casually, like my dick hadn’t just been in her ass.
“Thanks you too. And thanks for the encouragement. Anal virgin over here.”
“Me too,” she said with a coy wink.
“What!?” I asked. “That was your first time getting fucked in the ass? You’re lying.”
“Nope. I just knew if I told you that you would psyche yourself out even more. But I’ve been wanting to try it, and I just wanted to do it with someone, I, you know, trusted.”
I smiled, it was actually touching, in a weird way.
“Wow. So what’d you think?” I asked.
“I think it’ll take some practice to get 100% right, but I’m down to. You going to be home for Thanksgiving?”
I smiled, nodded. “Of course.”
Source: reddit.com/r/gonewildstories/comments/9q7y7j/pt_2_amazing_sex_with_my_first_kiss_more_than_a
Can’t wait for that story too. Thanks for sharing