Straight man's first time with a guy [MM] | 2016

So I'm a 30-something guy and have a thing for straight men trying out guys for the first time. The following is a true story from a couple hours ago. Hope it turns on a straight curious or bi guy somewhere. ;)

So I posted a CL ad offering to allow any straight guy to dip their toe in the water with a guy. I promised I would show them how to clean up their hole, finger and toy them, and help them cum while doing that. Met a nice straight married fireman about my age who was nervous but agreed to meet up in a hotel room. Tan skin, kind of dark sandy hair, pretty masculine body, a few extra pounds on him. He said his wife was abused as a child so as a result she wasn't very wild and he needed to explore some fantasies. You never know, but I believe I was his first man.

So we get there and shake hands and he's not sure what to do. So I kind of coach him on how to clean up his hole and send him off to the bathroom. He comes back clean and I start to rub his neck and back and shoulders through his t-shirt. I ask him to take off his shirt and jeans. He's got a wonderful patch of chest hair between and across his pecs and his nipples are hard, so I run my hands through it and play with them a little. He's a really meaty, burly type build. I've kind of made up a spot for him to sit on the bed against the headboard, and I get him to sit down.

So I just kind of gently rub around his body, his arms and chest and tiny guy and legs until my hands wander down to his underwear (boxer briefs). I gently brush against his dick, which is semi-hard. He's very nervous and is just kind of sitting there. I ask him if he's ok, and he says yes. I pull the elastic waist band down and pull out his dick. He's not very long, maybe average, but super thick. And his balls are a sexy shade darker skin.

So I just kind of gently rub my fingers along his dick and softly jerk him, trying to wake him up a lil. I think he's just really nervous so he's not getting very hard and he says he feels exposed and asks me to undress to even things out. So I take off my jeans and hoodie. I've obviously got wood showing through my boxers briefs. I'm not very thick, but average or a little longer.

So I have him lift his legs up, warm up my hands, put a little lube on my finger, and start rubbing circles around the outside of his hole. He says it feels really strange. I slide my middle finger inside him--it takes a second because he's not moving to accommodate me--and curve it up to locate his prostate and just start rubbing and massaging it. He's getting a little harder and I take my other hand and start to jerk him off. I check in with him and ask how he's doing, and he says it feels really strange but to keep going.

After doing that for a few minutes, I get out a vibrator and lube it up and slide it into his ass. Frankly I'm a little tired of the position lol. He's still only 3/4 hard, so I decide to really help. So I start to lick and blow him while pressing the vibrator so that it will make as good of contact possible with his prostate. He gets pretty hard then and I can feel his thick shaft in my mouth throbbing with blood. He's silent and kind of unmoving. I started getting tired of blowing him with no reaction so I lubed up his cock and jerked him with the vibrator in. Pretty soon he was saying how good it felt and asked if he should cum. I told him sure. I can tell he's getting close and then this huge stream of very white thick cum shoots about two feet in the air straight up and lands back on him and my hand. He probably had two or three convulsions. So I'm grinning huge and just gently rubbing the bottom side of his dick until I pull out the vibrator and help him clean up.

He doesn't move or say anything and again I feel like he doesn't know what to do. So I ask him if he's ever touched another man's cock. He says, "no." I ask him if he'd like to, and he silently reaches over, slides his hand through the leg hole of my underwear and starts slowly tugging on my cock head. I'm very hard and it feels great so I'm sighing in pleasure and I'm thinking he's intrigued by it. I stop him for a second and take off my underwear.

I'm spread nude on the hotel bed before him now, lying on my back, my dick straight up in the air, and he's above me and resumes slowly jerking me. So I ask him if he's ever explored another man's body. He says "no" again. So I take his hand and place it on my nipple, which he circles and flicks and pinches for a few seconds. So a little later I take his hand again and start rubbing the hair on my chest and my treasure trail. Again, he just kind of rubs it where I set his hand for a few seconds. So then I move his hand to my balls, which he fondles for a little while. Finally, I take his hand and start moving it toward my hole.

I can tell he's nervous and reticent. But he lets me do it--I set his hand next to my hole and he takes his index finger and gently presses in and out on my hole. I pull my legs up to my chest and kind of reveal myself to him and he keeps toying with it very shallowly but then says that's too much and stops.

I grab the lube and squirt a lot of it in a stream down the underside of my shaft and ask him if he wants to make me cum. He says ok and takes me again. He rubs the lube in with his large hands and jerks me until I'm really hard again. I'm moaning in pleasure and he's into it and I tell him I'm about to cum. I could tell he was both really into it and terrified, but he starts jerking faster. I came buckets of cum all over my chest and his hand. He reached for the towel pretty fast to clean up his hand but I just kind of lay there exhausted.

I asked him if he wanted to cum again, but he said no. I think he was still processing, but I know he liked it. He asked if we could do it again sometime. I told him maybe. I asked him if it was really his first time with a guy. He said yes again. He told me a story about going to a glory hole that was advertised as being with a woman and realizing right away it was a man, but not leaving. But other than that, I was his first man.