Bob and I had been chatting for about a year now, on a private Discord server. He was just about as curious about same sex relationships as I was. He was only about five years younger than me, and both of us had thought ourselves to be straight, most of our lives. I had been curious since a young age. Having had near experiences now and then that made me wonder. Not to mention I was one of those youths that always thought about how great it would be if I could suck my own cock.
Bob, on the other hand had been strictly straight, and only recently begun wondering after watching some Trans Porn. Chicks with Dicks fascinated him. Then he began to wonder what the difference would be if it was just a guy, instead of a guy transitioning.
We'd traded fantasies and what we thought it might be like. I had related my experience in having had experiencing being pegged by an ex some years ago. In case you're wondering, 'Pegging' refers to a guy being fucked in the ass by a woman wearing a strap-on dildo. Yeah, I'd allowed it, so I could fuck her in the ass. I can't say I hated it. As a matter of fact I kind of enjoyed it. Which only fed into my desire to feel the real thing. I even told Bob, that I'd been wanting the real thing for a while now.
We'd shared pics of our equipment and drooled over the thought of tasting each other and fucking each other. Even had a mutual masturbation session over Discord. I even got him to buy and try one of my favorite masturbation toys. A vibrating cup that fit over your cock and massaged you like a mouth. It got to the point that I'd begun having dreams about him. Even fantasized about my first time being fucked by another guy, being him. How it would feel and how I'd react.
We lost touch for a while. Then one day, out of the blue, I got a notification on that Discord server, that I hadn't logged into since the last time I'd chatted with him. He was on a business trip out my way, and wanted to know if I'd been serious about meeting. Ok, I admit it. Panic set in. I didn't respond. Would he go away if I didn't answer? Then I began to wonder again, what if I did respond, what would happen.
Finally, only a few days after the message came in, I responded to him. I told him I was serious and asked when and where he was planning on being. He forwarded me his itinerary, and asked me to let him know exactly what part of it was closest to me. I gave it a once over and found he would be staying at a Hotel about a mile from my house, two weeks from now. So I relayed that too him.
So the plan was set. We'd meet the day of his check-in and have lunch. Anything more we'd discuss over lunch and plan out from there. From that day, until our meeting, I was on edge. Nearly having panic attacks daily, and masturbating furiously to calm myself down over and over. This would happen, I thought. One way or another, this would go down and I'd finally feel what I'd been wanting, for a very long time.
On the morning we were to meet, I spent an inordinate amount of time on hygiene. Showering, shaving. All over. Even had the presence of mind to do a few enemas and clean myself out from the inside as well. Pocketed a handful of condoms and eventually headed out to our meet up. I arrived at the iHop in front of the Hotel and upon walking in, was flagged down. Bob had recognized me as I came in.
"Dave!" he called out across the restaurant. "Over here." he gestured. So I walked over to the table and held out a hand.
"Bob." I began. "Good to see you." Casual, nothing different about meeting anyone else, I thought. No need to get weird about it.
"I ordered already." he confessed. "Do you want anything?" I told him I'd had a late breakfast, and coffee would be just fine. I suppose, if I was honest, I was too tied up in knots about meeting a guy I would be having sex with, to eat. I'd probably puke it all up.
The whole conversation was pretty G-Rated. But there were a few comments, made under his breath that he just couldn't keep inside, I suppose.
"I just have to ask." he said in a conspiratorial whisper. "You really thought my cock was that good looking?" I'd almost had a swig of coffee in my mouth, and coughed one pulling the cup back from my mouth.
"Yeah, Bob." I responded in a low voice. "I really do." and explained, as I had the first time he'd uploaded a picture of it, that it was what I considered the perfect shape and length. I could see the smile on his face as he just nodded and shoved another bite of sausage and pancake into his mouth.
From there, the conversation was light, and eventually he said. "So, I don't have any work until tomorrow morning." His tone casual. "The company isn't tyrannical enough to put my to work the same day I just drove five hundred miles." he finished with a small chuckle. "You got anything going this evening?" he asked and looked up directly into my eyes.
"Not a thing." I replied. Sensing where this was going, and bracing for the question.
"Care to spend the night?" he asked. Well, I wasn't quite ready for that. I had been expecting something along the lines of 'wanna fool around this afternoon?' Somewhat surprised, I cocked an eyebrow at him and then grinned.
The next words out of my mouth were not intentional, but would set the tone for the rest of the night. Without conscious thought, I confirmed to him, everything we'd talked about in regard to my desires for trying a same sex relationship. My desire to be the bottom. I'd topped so many women, I'd given anal sex and hadn't felt much difference from woman to woman. But the experience of them doing it to me was new, and I'd told him I wanted to try the real thing. And so I answered in a very smart ass tone.
"Why Sir,!" I said, puffing out my chest. "Just what KIND of lady do you think I am?"
Bob laughed, and said. "So, that's a yes then?" I just grinned, lopsidedly, and nodded.
At that moment, I was really aware of what would happen, and still had some reservations. But I was into it now and the apprehension was turning to excitement, and I found I was looking forward to seeing what the evening had in store.
With the check paid, e went up to his Hotel room, and put out the 'Do Not Disturb' sign.
"Join me for a shower?" Bob asked. And now was the last chance to back out. But I didn't. In answer I just began stripping and laying my clothes over the back of the chair in the room's closet. Bob grinned and did the same.
I had seen pictures of Bob, prior to this. But standing this close in the shower, I got a real closeup of what was only a picture on a computer monitor, prior to today. Ok, I'd been in showers with other guys in my life. Back in high school, when I had been a volunteer for a fire camp in the national forest for a season, at the gym. But this was very close quarters and the warm water only helped intensify the heat coming off both of us.
Bob reached out a hand and rested it on my chest. I looked up at him then saw his gaze drop. I felt my cock twitch as I realized he was looking down at my package. Then he looked back up in a questioning manner. So I nodded, and closed my eyes. The palm of his hand was kind of rough, but the water allowed it to slip smoothly over my chest, and down over my abdomen.
He stopped briefly just below my belt line, and my cock twitched again. Then I felt his hand wrap around my length. Now, I'm not a big guy, but I'm not tiny either. When I'm hard I'm about five and a half to six inches long. I'm circumcised and my shaft is pretty smooth. The head is slightly oversize and really quite sensitive. Bob's hand fit around my shaft from the base to the head and the head rested in the crease between his thumb and forefinger.
