[MM] – Married guy’s first. Craigslist hookup on biz trip

I’m a late-30s married guy. Live in suburb of a conservative Midwest city. Been married 12 years and with my wife for 16 – since college.

I’ve fantasized about being with guys since I was teenager, but didn’t act on it until my late-20s. I would say I fall somewhere in between being bi and straight. Most of the time I’m more interested in women, but every now and then I get the urge to hook up with a guy.

I’ve been trying to sort out my feelings/thoughts about sex and my sexuality, so I thought it would be helpful to jot down all of my memories of my experiences with guys.

I’m going to do them one at a time. Since I love reading gonewild stories on Reddit, thought I would share them.

I’m happy to connect with anyone who is interested via comments or PMs.

Here’s my first experience with a guy –

It was about 10 years ago. Wife and I had been married for a few years, but didn’t have kids yet. I had a job that required me to travel 2-3 nights per week out west.

At some point, I discovered Craigslist. Most nights I was on the road, I would go to a bar in the evening for dinner and drinks and then come back to my room alone where I would watch porn and browse CL.

I would usually start by browsing the W4M section, but if I was drunk enough, I’d end up in M4M by the end of the night.

One night at home, I was planning an upcoming trip to a very small, rural town out west. I figured, “what the hell…” and posted an ad in the M4F section of Casual Encounters.

(To this day, I’ve never cheated on my wife with another woman. In fact, posting this ad is the only time I can remember of even attempting to cheat with a woman.)

I didn’t get any responses from women, but I did get one from a man. He was an older lawyer who was staying in that town to research a civil case. He was bi and looking to hook up with another guy.

My first instinct was to delete the email without replying. I was curious though. So I replied and we had a pretty friendly exchange that ended with him giving me his cell number and telling me to text him when I was in town. Let’s call him John.

I arrived in town, had two days of meetings with my customers and never called the guy. On my last night, I went out to grab dinner and then stopped in a local bar next to my hotel that had a band.

Sat at the only open seat at the bar and the guy next to me immediately started conversation. He was about 5’8 or so, about 6 inches shorter than me. Late-30s/early-40s.

We talked for a bit. He was a lawyer. In town researching a civil case. Was stuck in town for 6 weeks and bored out of his mind. I suspected it was the same guy so I didn’t give him too much detail about me.
As I got up to leave, he said it was time for him to go too. We walked back to the hotel together (the only decent one in the town) and went our separate ways in the lobby. Before parting, he shook my hand and introduced himself as “John.” He never put it together that I was the guy from the emails.

When I got back to my room, my head was swirling. Part of me wanted to call him, tell him it was me, and have him come to my room. The other part was terrified to take this leap.

I ended up taking the middle road. Sent him an email telling him that I was the guy he just talked to in the bar, that I was extremely nervous, but I wanted to connect if he was up for it. And I gave him my room number.

I didn’t get a reply email. Instead, I got a knock on the door within about 3 minutes of my email going out.

He had changed into gym shorts and a tight t-shirt. He had a fit, muscular body and I could see a definite bulge in his shorts.

I opened the door and he came in. There was some extremely awkward conversation before I asked him if he wanted a drink. He declined and said something along the lines of, “why don’t we just get straight to business.”

We went to the bedroom (it was a two-room suite) and stood on opposite sides of the beds. He was getting undressed, so I followed his lead and did the same. He was in great shape. Lean, muscular, little body hair.

We got down to our underwear and laid on the bed next to each other. He made a comment about how I did’t have to be nervous and I didn’t have to do anything that didn’t feel comfortable. That helped and I just went with his lead.

He climbed on top of me and started kissing my neck and and shoulders and nibbling on my ear. We both had our underwear on, but I could feel him grinding his dick against mine.

I was instantly hard. In fact, I was kind of shocked at how fast my dick went from 0 to 100. I started kissing his neck and rubbing my hands over his back. It was such a different sensation to feel masculine muscles rather than a woman’s softness.

Eventually I worked up the courage to slide my hands down his back and into his underwear, grasping his ass. I massaged his ass cheeks as he grinded against me, partially sliding down his underwear so his hard dick poked out of the waistband.

He kissed down my chest and stomach until his head was just over my dick. He pulled down my underwear and my hard cock sprung free.

“This okay” he asked, and I nodded.

Then he lowered his head and took my dick in his mouth. Honestly, it wasn’t the best blow job ever. He kind of jackhammered his head up and down and it was rough and aggressive.

Either way, it was super hot. It wasn’t long before I was ready to blow. I told him I was going to cum and buried his head down and took my full load in his mouth. It was a massive load and it ended up leaking down his lips and his chin.

He stroked my until I was done cumming and I was soft again, then excused himself to clean up his mouth.

After a minute he walked out of the bathroom and laid back down on the bed. He had a massive erection. About 7″ long, but pretty thick. It stood in the air at full attention, the obvious elephant in the room.

He clearly wanted me to return the favor, but I didn’t have enough courage for that. It didn’t help that I had already cum and wasn’t as horned up.

I stroked it a little and offered a weak apology that I wasn’t ready to give a blowjob. He was cool about it but asked if I could lay there naked and touch myself while he jerked off.

I figured it was the least I could do since I wasn’t reciprocating, so I started rubbing and stroking my soft cock. He got on his knees on the bed and stroked his dick while watching me touch myself.
Soon, he climbed in between my legs and started rubbing his dick against mine. He was stroking harder and faster and suddenly, a huge rope of cum shot across my chest and stomach.

He kept stroking as he went soft and a couple more smaller streams landed on me. When he was done, my torso was completely covered in cum.

I wasn’t quite prepared for that, but the feeling of getting cummed on was thrilling. I liked something about being used and being submissive in that way.

He got up and got dressed while I laid there naked, not quite sure what to do next. As he dressed, he offered some words of encouragement that I shouldn’t worry about this, not to freak out about it, and that it’s way more normal than I think. He also told me to be careful on Craigslist because there are some weirdos out there.

And then he was gone. I showered, jerked off while replaying it in my mind, and went to bed.

I stayed off Craigslist for a few months, but then gave in. I’ll describe that one in the next story….

Source: reddit.com/r/gonewildstories/comments/5j8ba2/mm_married_guys_first_craigslist_hookup_on_biz