Last Friday I went to a party. It was a last minute thing and it turned out to be a fun gathering. At the party I met this guy. Kinda of hard to describe but I'm sure you've seen someone like him before. Somewhat clean cut. Nice looking but not a head turner. He was wearing jeans and a t shirt. I could tell he had a decent body just the way his clothes fit. He wore glasses. Of course he works in finance. But he wasn't geeky or nerdy. We talked for a long time. He was a super nice guy. Great smile and his eyes kinda lit up when he smiled. Sunday night he sent me a text and asked me if I'd like to get dinner on Monday (last night). He got my number from a mutual friend. I was interested so said yes.
I met him at the restaurant. Dinner flew by. There was no shortage of conversation. We were at the table for a little over two hours. The more the evening progressed the more I was attracted to him -- and I wasn't drinking. LOL After dinner I offered him a ride home (he had taken an Uber). We got to his place and he asked me to come in to get a book he just finished reading and that we had talked about over dinner. I have a rule that if I'm into a guy I don't have sex with him on the first date even if it's just jacking off together. So I went in just to get the book and maybe a kiss on the way out.
We walked into his house. It was nice -- neat and tidy just like how I imagined. He didn't offer me offer me anything so I figured this was really just to get the book. I stood in the living room while he went to the bedroom. He came back out, handed it to me and told me not to worry about returning it, that he likes passing books on after he's read them. I thanked him for the book and told him I had a really nice evening and was glad he asked me out. He said the same. I told him I'd like to see him again if he'd be up for it. (The other guy's response at this point is usually very telling -- but that's another thread, lol.) He smiled, his eyes lit up and he said he'd really like that. It seemed genuine. There was a bit of awkward silence as we smiled at each other. I then told him it was getting late and that I didn't want to keep him up. I asked him if a kiss good night would be appropriate. He said, "Absolutely."
We leaned toward each other and kissed, lips to lips. It was one of those kisses where you know immediately you're really into the guy. We stepped closer, put our arms around each other, onto each other's lower back and kissed again. Just our lips, no tongue. We pulled back and he said, "That was really nice." I responded, 'I agree." Our crotches were pressed up against each other and I could feel his cock getting hard and knew he could feel mine. We kissed again. It was crazy good, our lips passionately communicating. We then introduced our tongues. It was perfect; he knew exactly what to do with his tongue, not like a serpent trying to find a mate in my mouth. At his point I could feel precum oozing out of my cock. We pulled back. He told me the kissing was better than he expected and said he had been thinking about kissing me while we were having dinner. I admitted the same.
I told him it was a nice evening and that it was a "school night" and I should get going. He acknowledged the same and walked me to the door. As he opened the door I thanked him again for the book. He smiled and said, "Sure." He told me to drive safely and leaned in to kiss me. That was the trigger. We pulled each other in tightly, closed the front door, the book dropped to the floor, hands went everywhere, feeling each other's ass and crotch. We led me to his bedroom. We immediately started undressing each other while kissing. I unbuttoned and unzipped his jeans and went into his boxers. I felt his thick hard cock and big smooth balls. He felt my cock and balls, his roaming hands driving me crazy. We then completely undressed. I knew he had a nice body but was surprised by how fit he was. And his hardon pointing up toward the sky was hot! He told me how good I looked naked and I returned the compliment. We got on the bed and it turned into full blown sex. Lots of making out, lots of oral -- nipples, cock, balls and ass. We 69'd for a long time, sucking each other's cock, eating each other's ass, sucking on each other's balls, fingering each other while sucking each other's cock. We then fucked each other, several positions, ending with me fucking him on his back, him cumming, then me pulling out and cumming on his chest and stomach. I collapsed on him and we kissed while our cum mingled between us. He told me he had a really intense orgasm. I told him I felt really connected to him during sex. We kissed again.
We then went into the bathroom and cleaned up. He asked me if I'd like to spend the night since it was so late. I looked over at the clock on the bathroom counter and was surprised to see how long we had been having sex! I told him I'd like to spend the night and that I liked being with him. He smiled. We got into bed, snuggled and fell asleep. I woke up in the middle of the night. My hand roamed his body. I placed my hand on his soft cock and he rolled over to me. I felt his cock until he was rock hard. He told me how good it felt. I told him I wanted him to fuck me. He rolled on top of me and we kissed. He then went down and sucked my dick. He placed his hands behind my knees, lifted up spreading my legs and ass and dove in, rimming my hole. He then stuffed his thick cock in my ass and we passionately fucked. It was the best middle-of-the-night fucks I've had. After cumming we went back to sleep.
This morning we showered together, sucking each other off and swallowing each other's load. He shot a big load in my mouth and his cum tasted amazing. We ran out the door with coffee in insulated tumblers and a banana. I'm in the office, typing this while on calls, wearing the clothes I wore last night. I'm tired from little sleep. I also have mixed feelings -- feeling good about the connection but sensing I may have messed up by going so far on the first date.
I sent him a text telling him I had a nice evening. Just a few short sentences. I received a one word reply, "same" -- no punctuation, no emojis. It kind of fell flat for me. And now I'm analyzing everything. And feeling stupid. Duh, I've been here before. The sex was awesome. But did I ruin it by having sex with him? I really wanted to see him again. Did he have sex with me because he didn't want to see me again? I've never had sex on the first date with a guy I ended up dating. Ugh.
I know. Keep positive. Don't over analyze. It's too soon. If it's meant to be it will happen. If not, he was a nice guy and the sex was really good.
Ugh... again.
