I finally did it
I’m (31M) currently in Nashville for work, which always gets my juices flowing being in a hotel room. Only problem, is my cheap ass company makes us room with whoever else is on the trip. On this trip, my roommate is definitely not someone who I’d get lucky with, lol. Anyways, his trip is 2 days shorter than mine, and left yesterday afternoon. I couldn’t wait for him to leave.
Literally as soon as that door closed, I locked the door, opened my stash pocket of my suitcase and pulled out my jock, plug, lube and a couple of condoms. Now, I need to say that until last night, I’ve never done anything with a guy before. I’ve been “that guy” on Grindr for forever - just scrolling, chatting, trying to work up the nerve and backing out.
So, last night, I load up Grindr and start scrolling. Get a message from a guy 0 ft away so obviously in my same hotel which is a huge plus. He’s 56, also traveling for work, and sent me some pics of this gorgeous cleancut cock - I’d say about 7 inches and a little on the thicker side. In his pics he was wearing a cock ring and he looked so hard and juicy. I told him it was my first time and I wasn’t sure how I’d fair taking a cock on the bigger side for my first time, and he assured me we would only do what felt comfortable to me. He instructed me to leave the door open/cracked, lay on the bed face down in my jock strap, and he would do the rest.
So, I laid down and told him my room number. My heart was absolutely pounding. I actually started shaking like I had the chills which I’m guessing was just adrenaline or something. I almost jumped up and said no thanks I changed my mind when I heard that door open but I just laid there, frozen. I heard him get undressed and heard the sound of what sounded like him popping a cap to a bottle. I glanced back and he had brought some coconut oil with him. New for me but let me tell you, I’ll be buying some when I get back home, ha!
He started to give me a massage and I just felt all my stress melt away. It actually felt so fucking good. I was getting more and more turned on the more he rubbed, and almost came when he crawled on the bed and straddled my ass. I could feel his cock between my cheeks as he continued to rub my back. I couldn’t help myself…I started lifting my ass into his cock and almost squirming for him to keep going. He started to kiss the back of my neck and worked his way down my back. When his tongue touched my hole for the first time…..I knew something flipped inside of me. I’m not a “small guy” by any means. I’m 6’2 180 and very fit, but in that moment it was like I was a 5’3 120 lb femboy just dying to get fucked. He fingered me for a minute which I actually wasn’t too into, it just didn’t feel like I thought. But…after that, he put a huge dollop of oil on my ass and I heard him rubbing his cock. He started saying “Good boy, you ready for daddy’s cock?” And I was just moaning “mmhmm” lol…didn’t know what to say.
I felt the pressure of his cock on my hole and what felt like the tip go in. He told me to relax and try to open up for him but it was like I was quenching involuntarily. He just left it like that for a minute or so but eventually I felt everything sort of relax and he slowly started pushing it in more. It honestly didn’t hurt at all, but it didn’t feel “good” is the way I’d describe it. After a few minutes he was stroking pretty consistently and all of a sudden it felt fucking amazing. I started moaning like a cock drunk slut and telling him to fuck me. It was so hot and felt so good, I was more than surprised. I was on all fours at this point and felt like I was getting close to cumming, but he reached around and literally as soon as he touched my cock I came more than I have ever cum in my life. He lifted me towards him and was kissing the side of my neck and I was in heaven. He said he was gonna cum and I started slamming my ass back into him. We fell forward and he pinned me down and came in me.
It was honestly amazing. Definitely felt weird down there afterwards but I guess that’s normal? I’m just happy he was very nice and respectful - I couldn’t have asked for a better first time. I would say that I am planning to go again tonight, but my ass feels pretty sore, haha. Anyways, thanks for reading.