My First Time

This tale depicts unprotected sex between two men. Such stories are fun to read, but actual sex in the real world should include reasonable caution and safeguards.

I had struggled with my sexuality for many years. I enjoyed viewing gay porn, and masturbating while watching, I browsed several gay dating and hook-up sites, I even bought toys and put them up my ass, but I never could take the plunge and meet another guy. I was too fearful of being seen, of being discovered. So I stayed deep in the darkest corner of the closet, and tried to be content with my fantasies.

I was alone at work, busy on a job, when I heard the door open. Walking out to the reception area, I discovered Roger, an acquaintance from high school days. I recalled he was a nice guy, but on the small side, and hung around the girls most of the time. I saw he was still short, shorter than my 5'7", but had filled out, was now broad shouldered with a barrel chest, tapering down to narrow hips. His blonde and silver hair was in a trim crew cut, and he had a small neat moustache. He was well-dressed, and had a confident air about him. We greeted each other, and asked what brought him back to town. I noticed his handshake was strong, and he held my hand as he replied.

"I'm here to check on my parents' place. We've moved them to a retirement home, and we plan to sell the house. I saw you were open, and wanted to say hello." Roger released my hand, but still held me with his gaze.

"The rest of the staff are gone for the day, so I'm holding down the fort. But I'll be happy to tell the boss you stopped by. What are you up to these days?"

"I drive for a delivery company, and have one of the routes inside the city. My boyfriend owns a retail shop, and we just bought a place out by the strip malls." He said this in a very matter-of-fact way, but was giving me a curious look at the same time, like he wanted to see my reaction. For once I was on my game, and I didn't let it shake me, on the outside anyway. I had heard rumors that Roger was gay, and he just confirmed it. I was curious on my end also, wondering why he shared that with me.

"Wow, that's great, that's supposed to be a real nice neighborhood. How long have you two been together?" Roger seemed surprised, just for a second, but recovered quickly.

"Oh, it was some time after I took a job in the big hotel downtown. We met at a bar, and started dating. Like a lot of relationships, it started off with sex, and matured from there." He said this very casually, like he and I talked about sex every day. But, I was unsure how to carry on, so I made some inane small talk, and after a awhile, Roger shook my hand again, and left. I mentally kicked myself, he had given me an opening, to at least talk about it, and as usual I had been afraid to do anything. That night, I thought about Roger as I lay in bed. He was very good looking, and I felt my cock getting hard. My thoughts turned to sex, and I fantasized about kissing Roger, and then sucking his cock, jacking off as I did so, and shooting a big load of cum on myself. The next night, I lubed up a dildo, and fucked myself while picturing Roger behind me, his cock inside me.

A little over a week later, I was in the city for a conference. The weather deteriorated while I was inside, and I was dismayed to see it pouring when I reached the lobby. Making sure I had key in hand, I dashed for the car, only to get in and find it would not start. So, I ran back to the lobby, not sure what to do next. I was standing in the foyer, water running down my face, when I heard a familiar voice, it was Roger. He laughed when I turned around, and asked me what was wrong. I told him my problem, and he thought about it for a moment.

"This storm isn't going to let up for some time, and you may have trouble getting a garage to come out until tomorrow. You could get a room here, but why don't you hang on to your money, and come with me? We have an extra room, you can take shower and warm up, and I'll loan you a robe or something." Roger seemed genuinely concerned, and his offer sounded better than an overpriced hotel, so I agreed, and we took off for his car.

His place was very nice, and Roger was an excellent host, getting me a robe and towels, and showing me to a room with an shower. The hot water felt great, and when I stepped out was very relaxed, and happy I had the good sense to take him up on his offer. I walked out into the room, and didn't see him right away. He was sitting on the chest at the end of the bed, and I was startled when I lowered the towel and saw him. I also noticed he was naked, and laughing.

"Are you okay? Didn't mean to scare you."

"Yeah, shit, uh, yeah, I didn't know you were in the room, that's all. Uh, what are you doing?" I stammered, not sure where to go with my eyes. He had no problem, looking right at me, or rather, looking right at my cock. I glanced down, and my 6" cock was semi-hard, hard enough to stand away from my legs. I looked back at Roger, and he was smiling at me, and his cock was stiffening too.

"Waiting for you to get out of the shower." he said evenly. "I thought you might want to have some fun. Why don't you come over here and sit down?" he said, in a soft voice. I hesitated, not sure what to do. This was what I had fantasized about, but like always I was having cold feet. "Come on, I won't bite." he said. I dithered for a minute, and finally surrendered to the moment. I walked over and sat down, careful to keep space between us. He scooted over next to me so our legs touched, and put an arm across my shoulders. Now my cock was fully erect, so hard it almost hurt. This was no longer a fantasy, this was a real man next to me, his cock also hard and pointing at the ceiling. His face was next to mine, and I felt his lips on my neck, and I felt his other hand on the inside of my leg. I was shaking with both fear and excitement, and Roger pulled away to look at me.

"Hey, relax, you're going to like this." I just nodded, unable to speak. I turned to look at him, and his gray eyes bored into mine. This time when he leaned towards me, his lips touched mine, and I felt my cock jerk in response. I was passive, letting him brush his lips on mine, but then he slid his hand up my leg, and cupped my balls, and my cock jerked again, and a small gob of cum oozed out. I surrendered, and kissed him back. It was all so hot, I could hardly stand it, and I was afraid I was going to cum again, and not just a single spurt. Roger must have sensed it, because he pulled away and stood up, then helped me to my feet. We climbed into the bed, and the break in contact helped me settle down a little. We were laying facing each other, and started to make out again. It was so sexy and hot, kissing a man, holding each other's naked body, skin against skin. I became bold enough to let my hands wander, feeling his hairy chest, and letting my hand drift down to the muscular globes of his ass. Roger trailed kisses down my neck and onto my chest, sucking in one of my nipples. It was wonderful.

I wanted to feel his cock, and moved my hand between us, searching for it, and finding it pressed against mine. It was very hard, and I traced my fingers up and down its length while wondering if I had the courage to take it in my mouth. Roger solved that for me, getting up on his knees next to me, and leaning over me, pointing his cock at my face.

"Go ahead, lick it, or put it in your mouth, you'll like it." I looked at it, so near, a tiny drop of clear precum in the hole on the end. I did as he asked, and stuck out my tongue, licking at the tip, then circling my tongue around the fat head. Roger liked what I was doing, giving a groan and pushing his cock at me. My mouth was already open, and it slid in before I could react, coming to rest on top of my tongue. All I could do was close my lips on it, and give it a suck, getting more noises from Roger in approval. With his help and encouragement, I sucked and licked my first cock, and learned what pleased him. While I was working on him with my mouth, he had my cock in his hand, slowly stroking it.

I could have gone on, and was thinking he might cum in my mouth, but he had other ideas. He pulled his cock from my mouth, and had me roll onto my stomach with my legs spread. I felt him move behind me, between my legs, and I trembled with both fear and anticipation, thinking i knew what he was going to do, and not sure what to think. I felt Roger's hand caress my ass, and a cool liquid dribble into my ass crack. I relaxed when I realized he was just using his hand and fingers, and began to enjoy what he was doing. He started by working the lube into me with one finger, then two. That was followed by a thin dildo of some kind. I was used to dildos of average girth and length, so there was no pain at all, just the pleasant stimulation from an object gently fucking me. Next, I felt Roger moving up on me, with one hand on the mattress at my side, followed by something pressing against my asshole, blunt and thicker than the dildo. It slipped right in, and he let his body down on me so he was resting on his elbows. I realized what was in me must be his cock, and I was pinned under him, his to do with as he wished.

Roger began to slowly and gently fuck me while nuzzling the side of my face from behind. The feel of his cock as it moved inside me was amazing, so much better than a rubber toy. As he touched new places in me, my cock swelled and rubbed against the sheet, and the sum of all the sensations was almost overwhelming. I wasn't going to last long, but there was nothing I could do except enjoy the ride. Roger was getting worked up too, I felt his arms wrap around me and held me tight while he increased the tempo of his thrusting. It was too much stimulation, and I started to cum, shooting several spurts onto the sheet under me. It felt like it would never stop, I'd never shot such a big load before.

Then it was Roger's turn. it took him longer, but I felt him tighten his grip, and push deep into me, holding his cock there as his hot cum gushed out. He gave a few short hunches with his hips, then he was also spent. We lay in that position for a bit as we recovered, Roger on my back, and me laying in a puddle of my own cum. He pushed himself off me, and I went back for another shower. Under the hot water, the thought came to me, Roger had a boyfriend, where was he?

We talked for a while over coffee, and Roger answered my questions. His boyfriend, Chad, was away on a buying trip, and would be back the next day. Roger asked me to stay the night, he wanted Chad to meet me. With a wink, he said the three of us could have fun. I agreed, and slept with Roger that night, experiencing another good fucking laying on my side with Roger spooning me from behind. The next morning, Chad arrived shortly after breakfast.

Chad was an inch or so taller than Roger, clean shaven with short brown hair and dark eyes. He was a handsome man, and carried himself with confidence. I was instantly attracted to him. He was broad-shouldered with narrow hips like Roger, looked very muscular. As Roger told him about bringing me home, and having sex with me, Chad looked at me with interest. When Roger finished, he looked at Roger, then at me, and asked me if I wanted to have sex with him. No hesitation this time, I immediately said yes. Chad winked at Roger, and the two of us went to the bedroom.

I slipped out of the robe, and watched Chad undress. As I thought, he was well muscled, and as his boxers came off, I saw he was also well hung, a long thick cock swinging back and forth in front of him. We embraced, kissing long and deep with lots of tongue. No longer a passive newcomer, I was looking forward to letting this hunk have me. He cupped my ass and squeezed, pulling me against him, grinding his cock against mine. Once again, the heat of the moment was threatening to overtake me, causing me to cum before we had gone very far. I wanted to wait, to savor it, so I pushed away.

"Let's get in bed." I said with a smile, and he smiled back, waving towards the bed.

I lay down on my back, with Chad next to me. We resumed kissing and tongue play, and I could feel Chad's finger on my nipple, tracing circles around it, a very hot and arousing feeling. I put my hand on his head, and pulled him to me, kissing him with everything I had. Now I could feel his hand easing down over my belly, through my pubes, and on past my cock and balls, stopping when he reached my ass. His middle finger pressed against my hole, rubbing and massaging. I released my grip on his head, and dropped my hand down to find his cock. It was thick and warm in my hand, and I wondered how it would feel, it was bigger than any dildo I had tried. My stroking caused Chad to groan with pleasure and the cock to get harder. We were both really getting into it.

"Mmmm, I want you to fuck me." I whispered in his ear.

Chad leaned across me, grabbed a tube off the nightstand, and squirted some on his fingers. I lifted my legs, giving him room, and he smeared it on my asshole. It was warm, and felt tingly as it absorbed into the skin. Another daub on his fingers, and this one he pushed inside, working it around. Inside, the tingle was much more intense, making my cock stiffen. Next, he applied a thick coating to his cock, and still holding my legs up, shuffled into position behind me, my legs resting against his chest.

I felt the bulbous head of his cock press against my hole, and he began to push. I was surprised, there was no pain, I just felt a fullness when he got inside, and I wriggled my hips to encourage him to keep going. He obliged, pushing it in slowly, until I felt his hips against my ass and back of my legs. Chad was holding my legs against his chest for support, with my ass lifted off the bed, and in this position he began to fuck me. Slow at first, but with long deep strokes. Whatever was in the lube was working on me, my insides felt like on fire, and my cock was drooling a stream of precum. It must have been the same for Chad, because it wasn't long before he was fucking me faster, grunting every time he sank it home. Apparently he hadn't cum for a few days. That ended abruptly, he arched his back and thrust his hips against me, and let streams of cum fly, one after another into my eager ass.

He stayed in me until his cock softened and slipped out, then he flopped down on the bed. He laughed, and motioned to the other side of the room. I looked, and saw Roger on the floor on hands and knees, his ass pointing at me, the hole slick and glistening with lube. "I think he wants you." Chad chuckled. "Go ahead, give him a good fucking."

My cock was still rock hard, all it needed was lube, so I smeared it on, and went to Roger where he knelt on the floor.

After years of Chad's big cock, mine slipped into him easy. It felt great, very warm, and gripped my cock with gentle pressure. The lube had the same effect on my cock, and as I fucked Roger the burning tingle increased, bringing me to the edge quickly. I tried to hold off, but it was no use, and soon I was buried in him to the base, my cock twitching every time it pumped a string of cum into him. Roger returned the favor, flipping me over and pushing into my already slick hole, and giving it to me one more time. When he finished, cum was running out of my ass and I felt satisfied like never before.

After that first time, I was a regular visitor at their home, and we spent hours fucking each other, or swallowing cum. Eventually, I sold my home, and bought another close to the city. Chad hired me to manage one of his stores, and it was then that I was introduced to Kevin, a nice guy, a few years younger than I, who was also a friend of Roger and Chad. Kevin and I hit it off, and he soon moved in with me. Once in a while, we would get together with Chad and Roger, or we would swap and pair off with them. I often reflected on my good fortune, how a chance meeting during a rainstorm changed my life forever. I'm happy with how life has turned out for me, with a good job, good friends, and a great relationship.