My first time with a guy
I don't remember the specifics, but in January I saw a comment on a post on reddit that grabbed my attention. I DMed the guy regarding the comment and we began a correspondence. He was cordial and respectful, and came across as a stable, grounded, good guy. It was rather refreshing.
He was on a work trip out of his home state and had lots of down time in the evenings, so we filled it up chatting about work and our backgrounds, which were very similar (same religion, same university [take a guess], both married with families, many of the same experiences). Eventually it turned to sexting (hello, this IS reddit) and we both very much enjoyed it. He had taken all his toys with him on his week-long trip and we both had a lot of fun as he introduced me to the different toys and how he enjoyed them (I had never owned or used any toys by that point).
After chatting for a few days we moved the discussion to a much more reliable and dedicated messaging app, and sexting took off with videos and calling, lol. We also shared our real names with each other. We'll call him Steve (not his real name, duh).
I learned that Steve lived in Albuquerque, which was extremely serendipitous since I already had a trip planned to go to a music conference there in March. I didn't share this immediately with him, because, creepy, but eventually after a couple weeks of constant messaging I let him know I was headed up there relatively soon. Which of course added a not-small measure of anticipation.
We began chatting frequently through the day, every day, and then began calling and talking a few times a week on our ways to work, many times for over an hour each call. I felt very safe and comfortable with him.
March came both too slowly and too quickly. I was beyond excited to possibly meet up with Steve, but also terrified of that next BIG step. I was going to be arriving on a Thursday to bring up some larger equipment, a day earlier than everyone else, driving up with a buddy of mine who was also attending the conference. It's a day-long drive and it helps having another person with you. I personally booked a hotel for that one night since we were going to stay with the main group at other accommodations for the remaining 2 nights after. Steve would only have Friday morning to see me before needing to be home a little after lunch time. We had decided that having my buddy there was a good thing; we could keep things PG between us and not go too far, just pretend we were old friends from college that hadn't seen each other in years.
Well, two days before heading up there my driving buddy pulled out. Steve and I decided that we could still keep to the main plan, still exhilarated yet terrified of that next step, but we would play it by ear. You can guess how well that went, lol.
Steve showed up at my hotel the morning after I arrived, and it was RIDICULOUSLY awkward! We hugged and then just kind of stood there, awkwardly. I invited him to sit down in the desk chair and I sat in the corner cuck chair (seriously, what else are they for?) and we talked for a bit, heart's racing and not knowing what to do, lol. There was a lot of nervous giggling and stretches of silence, but lots and lots of genuinely smiling. We were hella awkward but sincerely happy to be meeting each other.
Eventually we decided to go on a hike at one of his favorite spots, since it's in the mountains and we both love hiking. He drove us together in his car about 15 minutes or so to the foothills of some of the mountains out there. The hike was awesome, but neither of us had the balls to grab each other's hand, or let alone kiss the other. I did manage the pinch his butt once when he was hiking right in front of me, haha, and I squeezed his bicep while thanking him for inviting me in the hike. We had a few late season snowflakes gently falling with some golden morning sunlight, which was a little romantic.
We had decided a long time before that that he would take me to a sex shop to get a toy, since I really wanted one. By this point I had bought a set of butt plugs, but nothing else. So after the hike we went to his favorite sex shop. I thought it would be awkward, but the workers there were super professional and we were the only ones there on a Friday morning. We spent a good 20 minutes or so discussing the different dildos and prostate toys and masturbators, which was low-key erotic and a turn on, but I kept my composure. We finally decided and he bought me a prostate massager, then last minute grabbed a cock ring, identical to one he used. He paid for it all, and we left.
At this point we decided to go back to the hotel to drop off the toys, I could check out of the hotel, and then we could go to lunch before he had to leave. On the way back to the hotel that awkward someone began creeping back in, so I filled it thanking him for the unnecessary, but very appreciated, gifts he bought for me, while placing my hand on his thigh. He, of course, said it was no problem and he was happy to buy me something. Now, this was the first time I had really made dedicated physical contact with him, and I decided to throw caution to the wind as my hand began to lightly rub his thigh, and eventually started sliding up. His breathing began to quicken and his hands began gripping the steering wheel like we were on the racetrack. I was deciding how far I was going to go when I suddenly felt his dick head through his jeans. Steve was already rock hard. This was the first time I'd ever done anything to another man's dick. I began to run my fingers and hand over the imprint of his cock as he began to moan and breathe heavily. I leaned over a bit and reached between his legs and gently rubbed his balls through his pants, then returned to rubbing his cock. As intense as that was, we decided we didn't want to crash going 65 mph on the interstate, so I decided to be happy with my hand on his thigh the remainder of the drive.
By the time we got back to my hotel we were both crazy horny. We parked on the side of the hotel and entered the side door, partially to hide the sex shop bag I was carrying, and practically to hide the tents in the front of our pants. We just made it in the door of my room before he started ripping my clothes off and we started making out. Now, Steve had recently been in a production where he needed to shave his beard, and at this point had been growing it back out for only about a week. I am so glad I have a beard myself because the razor burn he gave me was EPIC, albeit hidden under my beard.
The kissing grew more intense as I finally got his belt unbuckled, and his pants dropped to the floor. I pulled back from kissing him and dropped to my knees in front of him. I'll never forget sliding his underwear down, it catching on his erection on the way down, and then his cock leaping out at me as his underwear got free and dropped to the carpet. As his 7" cock bounced slightly in its freedom there was already of large bead of precum gathering on the tip, growing as his heart raced and his cock got harder in the open air. For a brief moment I thought about it. Then I grabbed his cock with my hand (first time I'd touched a man's dick skin-to-skin), then with my tongue licked that precum off, swallowed it, and then lost myself in sucking his cock.
We spent the next half hour rimming and blowing each other, switching back and forth. He is very vocal in all the right ways, so we turned on the TV to a random sitcom and cranked the volume up to try to hide the moans and groans and exclamations that he couldn't hold back. We were somewhat successful, lol. That just got me harder and more and more turned on.
As I worked on him I was in heaven, legitimately enjoying sucking his cock. Finally at one point his voice began rising to a crescendo, and I doubled down with the suction and speed. Once he started cumming I took every drop, then sucked and pulled out as much as I could and swallowed it all. He returned the favor right after. I'll never forget looking down, my hands on his head, as he worked my cock with his mouth. When I came it was the first time I had to shove anyone away from me, it got too intense. And yes he swallowed it all, too.
After that we just cuddled and stared at each other for about 15 - 20 minutes while the TV continued blasting.
Time, unfortunately, was against us, and I had to check out of the hotel and he would soon have to return to his family. We took more than a few minutes trying to find all our articles of clothing strewn about the room, got dressed, made out a little more, and then headed out to lunch. I let him pick one of his favorite restaurants that his wife doesn't like, lol.
Since we were back in public we had to put the straight masks back on. Lunch was great, and we continued getting to know each other and laugh over good food and company. After lunch was done and paid for we went back out to the parking lot to our cars and said a few more words. I gave him a good, deep hug them got in my car. We waved goodbye to each other a final time, then drove away in different directions.