First time…? – Fixed
Introduction:
I’m straight but curious, and this story is an imagining of how my first time may go.
Though I identify as straight, and have been married over 20 years, I’ve had a curiosity about engaging in oral sex with another man since I was in my teens. The urge to satisfy that curiosity has ranged from a mild, easily ignored buzz in the back of my mind, to an almost obsessive desire, but I never became motivated to actually try anything.
Well, that’s not entirely true. When I was 17, I did talk an older friend, who was bisexual, into having a go at it. It was nervous, adolescent fumbling on my part, and I think he just really didn’t find me to be his type, so nothing “came” of it (so to speak) for either of us. I’d had to have a good amount of beer to even get up the courage to do that, so my being inebriated may have had a hand in my not finding it particularly satisfying.
The urge had recently started building again to the point where almost all of my masturbation fantasies revolved around it. In my fantasies, I didn’t have a distinct person in mind; in fact, there wasn’t really even a face involved. I mostly “saw” a torso with a penis attached, and I licked and sucked the penis until it was over. To add as much realism to the fantasy (and because it has also always been a desire of mine to perform oral on myself), I would on occasion lay in bed and throw my legs over my head, rolling up in an attempt to suck myself. Of course I was never close, but I would masturbate this way until I came, and either let fly into my own face or in my mouth, at which point I would usually swallow some of it. I didn’t find the taste particularly pleasant afterwards, but in the heat of the moment it was what I wanted.
In fact, I often think that if I could actually suck myself, the urge to be with another man would probably go away altogether. But let’s face it; it’s easier to find a man to play around with (or so I thought) than to diet and exercise and become trim and flexible enough to suck yourself off.
Usually the urge would stay with me several days, maybe even a few weeks, but then eventually go away as other facets of life start taking over. But something was different about this time. For whatever reason, I was determined that this time, for good or ill, I would fulfill this fantasy. I was interested in seeing if the reality would be as exciting, once I was in moment. But how does a straight guy, with a reputation in the community to uphold, go about finding someone to satisfy this kind of curiosity with?
I turned to Craig’s List, and searched in the “Casual Encounters, m to m” section of the Personals. A lot of the ads were from aggressively gay guys who wanted to “ream” and “pound” and whatnot, and I just wasn’t interested in that. I was looking for someone more along my lines: married or attached, curious about oral (only), and willing to experiment in comfortable manner. I didn’t care at all about looks, and size wasn’t an issue as long as they were within a range of normal. I didn’t want a toothpick, but I didn’t want a salami either.
There were some promising ads, so I responded to a few with my stats (6’1″, 240, not really fat, but pudgy, 6.5″ cut, medium girth, etc). Most didn’t return my reply, and those that did would seem interested at first, then suddenly all communications would stop. I finally put out my own ad, and received a number of responses, which was encouraging. Most of them did not meet my criteria as I described above, but there were a few gems in the trash.
I had a promising conversation with a man who was also curious, and who’s wife wanted to watch us and maybe join in at some point, but that would be up to her. Once again, after some email and picture exchanges, they just dropped off the face of the earth. I was disappointed, because having a woman involved, even if she was only watching, seemed like a perfect bridge between what I was used to and what I wanted to do.
After that, there were a couple more false starts, and I eventually decided Craig’s List just wasn’t going to work. A lot of the ads ran over and over, and it just started seeming like most of them were insincere, or perhaps a scam of some kind. But I still had the urge.
Finally, I decided I would have to call in some expert help. I contacted a former co-worker, whom I knew to be gay, with the intention of asking for his advice on how to find someone that meets my criteria. Tommy (as he’ll be called here) didn’t meet my criteria, being openly gay (so definitely not straight but curious) and “married” to another guy. But I had the feeling from when we worked together that he found me attractive, and I hoped that he would have some insight on how to find the right situation. Perhaps, I reasoned, he even knows other married men who are curious and looking for a similar set of circumstances as I am.
I explained to Tommy that I’d like to meet him for a drink or something to get his advice, and he quickly agreed. So quickly, in fact, that I wondered if he had some clue, somehow, of what I was going to talk to him about. I considered the possibility that, when I laid out my situation to him, he might volunteer. At first the idea seemed a non-starter, not only for the fact that he didn’t meet my criteria, but I also didn’t know if he was really interested in my or not. And even if he were interested, being in a relationship with another man, I didn’t know if he would be the type to cheat.
However, as the days counted off to our “date”, as I’d started thinking of it, I realized that there were some other aspects of him that were appealing. We had a good rapport, and got along well. Plus, I just felt I could trust him, not only with the secret I would be revealing to him, but that, if we did do something together, he would respect my boundaries and not try to rush me or be overly aggressive. Besides, if he was interested, this would be perhaps the quickest, drama-free way to go about getting what I wanted.
On the day we met, my wife went to an event that I knew would keep her busy for at least three, and up to four, hours. Still, I had an alibi for being away from the house, just in case she came home early or called me to see how I was getting along. Everything was set, and I left soon after she did to meet Tommy. I was as nervous as I’d ever remembered, perhaps even more so than my first date as a teenager.
When I got to the grill, I looked around and spied Tommy at an out-of-the-way table in the back corner. This added to my suspicion that he had at least some idea of what the conversation would be. I approached and we said our hellos, shaking hands. I don’t know if he noticed how damp my palms were, but he didn’t say anything about it.
We made small talk as we looked over the menu. I finally ordered a beer and a burger, and Tommy ordered the same. When the beer was set before us, we raised our glasses to one another, and had a drink. With those social niceties out of the way, Tommy said “So, what did you want to talk about?”
Now I had been rehearsing how I would begin for the past week, and had gotten no further along in finding an appropriate manner during that time. I didn’t want to make it seem like I was asking him to have sex with me directly, but I didn’t want to be so subtle that he wouldn’t think to ask me if he would do. By this time I’d convinced myself that, if he was interested, I would take him up on it (providing he could guarantee me that he was free of any STDs.)
“Honestly, Tommy,” I began, “I’m not sure how to start. I thought it would just come to me and the words would flow, but that’s not the case. It’s… complicated.”
Tommy chuckled and said “Why don’t you try just coming right out with it? Say what’s on your mind as succinctly as possible, get it out in the open, then you can clarify any details that couldn’t be expressed in that first sentence.”
“Good idea,” I responded. I took a drink of my beer, and a deep breath, and said: “I want to have sex with a man.” If Tommy was surprised, he did a good job of covering it up. I searched his face for some idea of what he was thinking, but he just looked at me silently for about 10 seconds, then took a drink of his own beer.
“Do you have anyone specific in mind?” he asked.
“Not really, no.” I then explained about my past 30 years of desires and, basically, this whole story up to the point of contacting him. He sat silently, attentively, through the whole thing, only interrupted by the waitress bringing our burgers. I ate slowly, because I was doing all the talking, but my nervousness slowly subsided. Tommy was right; once I’d said the first sentence, the rest was easy and just filling in the details.
When I was finally done, he looked thoughtful for a moment, then said “I don’t mean to be presumptuous, but are you wanting me to be… that guy?”
“I’ve considered it, Tommy, but honestly I just don’t know. As I said, I was hoping for someone who, like me, has no real experience and is wanting to try something new. Someone who won’t be overly timid, but also won’t be aggressive and acting like I’m someone to be dominated over and conquered. We get along well as friends, and I know that, even though you’re gay, you aren’t flaming about it, which I think would be a total turn-off for me. I think it could work, if you are truly interested, but there are a number of things I’d want you to be clear about before we made that decision.”
“Like what?”
“Well, for starters, despite what I want to do, I am not in any way attracted to men. Not like I am to women. My curiosity notwithstanding, I don’t think of guys in a sexual sense. I think of the act, but it’s something I do to a dick, not to the guy the dick belongs to, if that makes sense. I just want you to understand that, this won’t be a romantic or sensual encounter for me. I don’t want a crass blow and go, but this won’t be tender and loving and sweet.
“I want us to have a good time, and for it to be exciting and hot. But for me, it won’t be like when I’m with a woman, and I want to pour over every part of her. I want to touch you and make you hard, then suck you until you come in my mouth. But, and I know this part will sound strange, I have no desire to kiss or hug or any of the things I would associate with sex with a woman. Does that make sense?”
“Well,” he replied, “it does. I think I see what you’re getting at. You don’t want a cold, clinical encounter, but you don’t want to make it into a courtship either.”
“Exactly! We’re friends, and for me this would be along the same lines as friends going canoeing for the first time together. They would know that, if the experience was fun, they might do it again, or maybe it’s just the one time. But either way, they’d still be friends, but nothing more involved.”
“Kind of a ‘friends with benefits’ thing, then.” he offered. “Okay, I think I can go along with that.”
“So, you are interested in helping me with this, then? To be… that guy?” I asked.
“Of course I am! I always thought you were hot, but I figured you were off limits. I’d love to be your first experience, and I’ll definitely respect your pace and boundaries.”
“What about Peter?” I asked.
“I’ll do anything to your peter that you want me to,” Tommy replied with a playful grin.
“Ha ha, asshole,” I said, laughing. “You know very well I mean your husband. I don’t want to have to worry about a jealous man looking to cause me trouble.”
Tommy smiled wanly, and said “I don’t want to go into it, but trust me; that’s not going to be a problem. When would you want to do this?”
“Well, I’ve never really been the patient type,” I answered. “I know you live near here, and I’m okay with now if you are.”
“Now is good for me. Oh, my god, I can’t believe this is actually happening!” Tommy said, almost breathlessly. “I’ve been wondering what you wanted to talk about, and fantasizing that it would be something like this, but I didn’t really think it would be. I was sure it would be something more along the lines of me helping you with a March-of-Dimes event.”
“Trust me, Tommy,” I answered with a grin. “You aren’t the only one who can’t believe this is happening. I’ve been trying to get the right situation to do this for so long, and now that it’s going to happen, I’m nervous as hell!” I wasn’t lying, either; my mouth was dry and my hands were starting to shake just a little. I would have considered having another beer, but I didn’t want to take any chances that my memories or perceptions of things would be clouded by the alcohol.
We paid, and I followed him from the grill to his house, just a mile or so away. I really had to work to settle my nerves on the ride over, and I guess he did as well. The first thing he did when we entered his house was give me a quick tour, ending back in the living room.
“If you don’t mind,” Tommy said when we got there, “I’m going to have a quick pee. There’s a guest bathroom just down the hall,” he added, pointing, then walked towards the back of the house where the master bedroom was.
I went into the guest bath and took a piss, my mind racing the whole time. I would just start to get a hard-on, thinking about what I was finally going to get to do, then the reality of it would hit and my dick would turtle. That got me anxious that, when the time came, I wouldn’t be able to get hard. Of course, for me this was mostly about my fantasy about sucking a cock so I didn’t actually have to be hard. But I like having mine sucked as well, and didn’t want to miss out on the chance when it was there.
I had showered before leaving, but decided to take the opportunity to “freshen up” a bit with a wash cloth hanging near the sink. It was mostly a formality, but I didn’t want an unexpected funk to greet us when I took my clothes off.
Holy shit! I’m actually going to take my clothes off in front of another man, and he’s going to be naked too. My mind was racing again, with quick flashes of what I thought would be happening soon. Tommy was similar in build to me, a little shorter and also pudgy (but not fat.) Looks wise, not that it mattered to me really, but he wasn’t ugly. I don’t know if he’d qualify as handsome, and certainly not hot, but neither do I despite what he’d said. I made a quick calculation of his features and figured his dick would also be similar to mine, which would be perfect for me.
I walked back into the living room, where Tommy was already waiting. “Would you like something to drink?” he asked. “Another beer?”
I was still tempted, again just to calm my nerves, but decided not to. “Just some water,” I said. My mouth was dry as sand. Tommy handed me a glass, then without saying anything started walking back to his bedroom. I sipped the water and followed. I entered the room just as he was turning to face me.
“I know you said you didn’t want to kiss,” he began, “and I don’t want to push anything, but are you sure you don’t want to try it?”
I had actually been thinking about that, too, and gave him my honest answer. “It’s not something that’s for me, but if you want to kiss, I’ll give it a try. Who knows, maybe I’ll like it once I get past the hangup.”
“I don’t want you to do it if…” he started, but I interrupted him. “Tommy, stop. At this moment, I can’t kiss you for any other reason than it being for you. It won’t be because I want it, because right now I don’t see how I ever will want it. But I’m willing to try it, for your sake, if it’s something you want to do. That’s all I can offer.”
Tommy considered my words for a few seconds, then said “Okay, I understand. Kissing is a big thing for me, so as long as you aren’t feeling forced into it, I’d like to kiss you. If you don’t like it, we don’t have to do it again, but I do want to at least just this one time.” He approached me slowly as he said this, and was right in front of me as he finished, looking up hopefully. He was a couple inches shorter than me, so I had to tilt my head to his, and when I did he leaned in and kissed me.
At first it was just a brush of his lips, but then his tongue darted out and tentatively licked my lips, as if seeking permission. I was reluctant at first, but then decided that since I had agreed to the kiss, I should at least give him the benefit of going all in. I pushed back my biases and pre-conceived thoughts about it, and opened my lips to him. And for the first time in my life, I kissed another man with abandon, tongues touching and lips locked together. The experience was… okay. Not great, not the breath-taking, knee-knocking experience of that first kiss with a girl. But I didn’t immediately feel ashamed or embarrassed, or like I needed to rinse with mouthwash and brush my teeth. I suspected that would come later, though, after doing what we came here for.
We broke away and looked at each other. I grinned to show him I wasn’t grossed out, and the look in his eyes showed that he hoped that would not be the last kiss. I could take it or leave it, but decided then that I would be willing to kiss him again since it apparently meant that much to him. I would even do it with a pretend passion.
“Let’s get undressed,” I suggested, pulling my shirt off. Tommy smiled and practically tore his clothes off, and was completely nude while I was still pulling my shoes off, my pants down around my knees. I laughed, and finally stood before him after pulling down my boxer briefs. I wasn’t completely hard, but at least I wasn’t’ turtled either. Tommy, on the other hand, was clearly excited, his cock hard and pointing up.
I looked him up and down, relishing being able to openly look at anther man’s junk. As I stepped closer to him, I noticed that his knees looked a little shaky, and that his hands were trembling slightly. I looked him in the eyes and, gesturing towards his dick, asked “May I?”
“Of course,” he answered, his voice quiet and hoarse with passion. I reached over and lightly touched his shaft, brushing my fingertips along it’s length. It jerked just a little when I first touched it, which made me grin. I gently reached under and groped his scrotum, playing with his balls the way I like. Not too much pressure, and no tugging, but a little pull and roll here and there. Tommy sighed as I did, so I figured I was getting it about right.
After a bit I went back to his cock, touching the shaft and then taking him fully in my hand. Again, I tried to be gentle but to move my hand the way I would my own cock, and before long was rewarded with the first drop of pre-cum. I didn’t much care for the taste of my own sperm, but I always thought the pre-cum was okay, and now I was curious if I’d think the same about another man’s. I had been staring at his groin this whole time, but as I scooped up the bead of moisture from his tip, I looked him in the eyes as I brought my finger to my lips and licked it clean. It tasted good, just like mine.
Tommy sighed again, and leaned toward me, then stopped, pleading for permission with his eyes. I nodded, and he closed the gap to kiss me again. As we kissed, I took him in my hand again and he began to fondle me as well. I had been so intent on his cock that I hadn’t paid any attention to mine, and was surprised to find myself almost fully hard. The more he played with me, the firmer I became. And I have to admit, the kissing was nice as well. It was like now that the barrier was broken, I could forget about my hangups about it and just let it happen.
Now, though, I wanted to get down to business, as it were. I broke the kiss and gently guided Tommy over to the bed. I wasn’t sure how I wanted to do this, and my indecisiveness must have shown. “Let’s both sit on the bed, and talk for a bit,” he suggested. “What’s going on in your head,” he asked, after we got adjusted. We were sitting cross legged, facing each other. We were both still very erect.
“So far this is nice,” I answered. “I was worried that I would be so nervous that I wouldn’t get hard, but I don’t think that’s a problem now!” I laughed.
“I see that,” Tommy said, also laughing. I looked down and noticed that I too was starting to leak a little pre-cum. Tommy mimicked me as he reached over to scoop up the moisture and lick it off his fingers. “Yummy!” he exclaimed.
I grinned, shaking my head. “You’re so gay!” I said, with mock severity. “Join the club!” he rejoined, laughing. Which kind of took me aback. I wanted to protest, and assure him that I’m not, in fact, gay. I’m not even bisexual; I don’t want a relationship with a guy, I just want to have sex with him. I realized how absurd that sounded, even if it is true, and decided it wasn’t worth trying to make the point. Besides, I knew Tommy wasn’t being judgmental, and meant no more slight from his comment than I had from mine. I just let it go.
“Let me just look you over a bit,” I suggested. “Just until I’m more comfortable.”
“Of course,” he answered, leaning back and opening his legs. I leaned forward, but realized that would be very uncomfortable, so I swung my legs around and lay prone in front of him, my face inches away from another man’s cock. Leaning on my elbows to free up my hands, I again took Tommy’s dick in hand and really looked at it. I moved it back and forth, looking at the way the veins ran together, the way the ball-sack hung from beneath it. I felt the thickness and the texture, the meatiness of it. I’ve become so accustomed to my own that I’ve really taken for granted how heavy and full it can be.
Tommy’s was, as I’d guessed, similar to mine, though he was perhaps a little longer (and in fact, we confirmed that later; he was a solid 7″), and not quite as thick. He had a thick mat of hair around his groin, but it was tightly curled and didn’t appear as long as it really was. More importantly, I wouldn’t be fighting through a jungle. (As for me, if I let my pubic hair grow, it would be a gnarly mess, as my wife has been so kind to inform me. I refused to shave after the first time, but I did trim it often to keep it very short.)
His balls were a little bigger than mine as well, but not by a great deal. All in all, I was pleased with what I was getting.
As I examined him, he’d actually started softening up a bit. (I could sympathize; if my wife was going to give me head, but dawdled too long for some reason or another, I would start to lose my erection. And if I felt like she was really stalling, I’d lose it all together and that would be that. Perhaps that was her plan. But I digress.) More pre-cum was at the tip, about to drip off, and without thinking I stuck my tongue out and licked it off, brushing the head. He was instantly hard again.
I looked at him, and the wide-eyed anticipation that he was looking at me with caught me off guard and I started laughing. He gave me a puzzled look, which made me feel a little bad, but I just smiled and shook my head. I looked back to his cock, took a deep breath, and decided it was time to go for it.
Without having any practical experience in these things, I just went with what I felt like I would want. I started by licking underneath his shaft, noting the musky (but not unpleasant) taste of his skin. I went a little lower and licked his sack, massaging his balls a little with my tongue. I was still holding his cock, and could feel it straining in my hands, so I gave it a little tug as I continued to tongue his balls and shaft.
I licked higher along the shaft, until I reached the sensitive area just below the head. I lightened my touch and barely skimmed that area, then resumed pressure right at the slit, getting another taste of pre-cum for my efforts. I swirled my tongue around the head, noticing the similar but slightly different taste here from the lower part of the shaft. Experimenting, I licked the shaft then the head again, confirming the difference. This time when I licked back up to the head, I kept pressure on the sweet spot, and as I reached the head I enclosed my lips around it and gently sucked. The gasp from Tommy let me know I’d done that part well.
When I opened my mouth wider, and slowly engulfed him with my mouth, he groaned. I could only get about three inches in before I felt the beginning of a gag reflex, but I knew that was just nerves. During the years of my having this fantasy, I’d practiced many times on object such as bananas, small cucumbers, and even a few of my wife’s vibrators and dildos, and I know that with patience I can take quite a bit without gagging. I backed off a bit, and slowly went down again, a little further this time. I repeated this process, and before long I felt the head hitting the back of my throat, and I was almost completely in. I took a deep breath through my nose, and slowly pushed until it was all the way in; my nose was pressed into Tommy’s groin, and just to show off I worked my throat a bit and stuck my tongue out to lick his balls.
He was leaking pre-cum like a hydrant, and I was drooling all over the place. Having proved I could deep throat his cock, I pulled back, and started performing a more conventional blow job. I bobbed my head up and down, slowly then quicker, then slowly again, while jacking him with my hand matching the movement of my mouth. I was single-mindedly determined to finish this right here and now, but Tommy had other plans. He grabbed my head, and pulled me up to kiss me. I didn’t have to work hard to pretend passion at this point.
“Jesus, are you sure you haven’t done that before? Because you’re a natural.”
Feeling pleased with myself, I said “I just did what I like having done to me.”
“Well, I like what you like! Let’s see if I can do as well for you!”
I leaned back and… well, basically he did the same for me, with variations, that I’d done for him. It was good, and of course I was going to want to come too, but this story is about me sucking his cock, so I won’t waste a lot of time describing what he did to mine. It was good.
After about 10 minutes of this, I wanted back at his cock. We scooted around until we were in a laying 69 position (neither of us on top), and as he continued to work on me, I once again took him in my mouth. I started slow, going as deep as I comfortably could, then backing off until he was almost completely out of my mouth. I was playing with his balls with my free hand as I continued to suck him, then I gripped him in my hand again and started picking up the pace. Tommy recognized my intent, and he picked up his pace as well.
I could feel my own orgasm building, still a ways off, but I was determined that Tommy was going to come, and soon. As much as I was enjoying the build-up, I wanted to finish this. Before long, I felt Tommy tense, and he started thrusting his pelvis towards me. My hand around his dick kept him from thrusting too deeply when I wasn’t ready for it, and the fact that I was having this effect on him got me closer as well.
Suddenly, Tommy groaned deep in his throat, sending vibrations through my cock that brought me to the edge. I groaned as well, which must have had a similar effect on him. Without it being my intent, we were going to come at the same time, and now there was not stopping it.
I tensed at the same time Tommy did, and just as the first wave of my orgasm started to crest, I felt Tommy’s cock swell and twitch, and suddenly I was shooting cum in his mouth while getting my own mouth filled. It was so similar so what I imagined it would be like if I could suck myself off, it was as if I were doing just that.
I was able to swallow the first three blasts, but it was coming quicker than I could manage, and by the fourth spurt it was dribbling out of my mouth, down my chin and on his balls and upper thigh. I kept at it, as he did me, and after another two strong spurts which I mostly, but not completely, swallowed, he relaxed. My own orgasm had subsided, and there was nothing left but the clean up. I took him out of my mouth and licked the cum that had overflowed off his thigh and around his balls, then licked his shaft and head clean as well. The flavor wasn’t any better than I remembered mine being, and I knew in a few minutes the after taste would hit and be pretty lousy, but at the moment I didn’t care.
I finished, and we turned and faced each other again, laying side by side. He kissed me on the lips, and I kissed back, but now the moment was over and I found myself having to try a little harder to show passion.
“What do you think?” he asked. “Was it good for your first time?”
“It was incredible, Tommy!” I said, truthfully. “I was worried it wouldn’t be as good as my fantasy, but honestly, it was every bit as good. Maybe better.” He kissed me again, but could sense my reluctance.
“I’m sorry,” I said. “Before, while we were into it, the kissing was fine. Good, even. I enjoyed it. But the moment is over now. I don’t mind it, if you need to kiss me, but now I’m not as into it.
“But I enjoyed that, and I think I’ll want to do it again. I’d rather it be with you instead of having to start looking for a compatible, comfortable situation again, but if you would rather not, because of my not really wanting the whole relationship thing, I understand.”
“No,” Tommy replied, “I understand and I’m fine with it. I will have a relationship with a like-minded person again some time.” I didn’t miss what he was implying, but decided to let it go for now. “I’m good with being your friend with benefits, and anytime you want to play, just let me know.”
“I’ll definitely do that,” I said, smiling.
