Straight Guy's First Time

This is a true story.

So, it's been a rough year for me. I ended my almost decade-long marriage, marriage that I had never been happy in. I had spent the past twelve months squabbling in court with my vindictive ex-wife over child support and the custody of our two children. I had a good lawyer, but he had taken me for every cent I had. Doesn't matter. You can't put a price on freedom, and only the unfortunate among you will understand how lonely it can get, being trapped in a loveless relationship.

I am a guy in his mid-thirties, 5' 11" tall on my best days and weighing 170 pounds. I'm decent-looking with a so-so body and as straight as they come. I have never found guys attractive, not even in the slightest. And yet, I had been having these crazy fantasies for a couple of years now of having sex with a dude. If I had to guess, I would say it's the product of years of watching porn.

The thing about porn is that it grows duller over time. Nowadays, I am barely turned on watching plain old vaginal sex. Or maybe I am turned on, but not to the extent that I'm looking for. It would take too long to really get myself going, and I was never the kind of guy who enjoyed watching porn for hours at a time. I pull my pants down, put some shit on, and five minutes later, I want to be relieved. It's sort of a chore for me, I guess. Like brushing my teeth.

With time, I found myself growing desensitized by porn. Conventional sex wasn't cutting it for me anymore. I needed something different, more exciting, even if I wasn't necessarily into that type of sex. So I had started watching gang bangs, cuckolding, BDSM, humiliation, grannies, midget chicks getting pounded, you name it... if it's on the internet, I've watched it. It didn't take long until I had graduated into some seriously fucked-up sex, all in pursuit of quick and explosive orgasms.

I guess that's when it really escalated for me, when I found myself watching trannies. I was really into it, as some of them are super-hot. At times, I can almost imagine myself being in a relationship with one. Moving on from trannies to full-on gay was quick and painless to my surprise. Again, I wasn't turned on by the guys. I was turned on by the taboo (and yes, most straight guys find gay sex taboo even if modern times dictate otherwise).

And so, after over a year of beating off to tranny/gay porn, I had begun to fantasize about having sex with a guy. More accurately, I was fantasizing getting fucked by a guy. I wanted to suck a dick, too, and swallow cum. Why? Your guess is as good as mine. I'm seriously not into dudes, and I would feel disgusted with myself the second I finished coming. But I did want to do those things, if only to satisfy this untamable want.

In my fantasies, I am always bottom and sort of feminine in my behavior. I would make up many scenarios of guys seducing me and such. My favorite is when I meet some dude in a club. He pretends to be straight, even though I know he's gay. He invites me to his place to chill with a drink. In his place, we would kick back on the sofa and watch some movie, and the guy would gradually scooch closer.

I'm always intoxicated in the fantasy, and the guy would make sure I'm pretty loaded before he makes his move, like stroking my shoulder or something. After he sees that I ain't stopping him, he would take it further, like kissing my neck and stroking my thigh. After a few minutes, he would unbutton his jeans and make me blow him.

While I am reluctant, I do it anyway, and do it right. I deep-throat him, tease him my tongue, look up into his eyes the way girls do. I'm so feminine in the fantasy, and I have no clue why, but it feels so good. When he comes in my mouth, I swallow. I also make those sexy humming voices while I take his seed down my throat. When he's done, he pulls me back up onto the sofa, and we make out.

My head is on the armrest, and he's on top of me, dry humping me. He's shirtless, and he takes my shirt off, as well. He pulls down my jeans and boxer briefs, and I let him, although I'm very nervous and apprehensive. He takes out the lube from the table drawer and coat his raging-hard cock. It is at this point when I put up some weak resistance, telling him I'm straight and that I'm afraid of being penetrated.

He doesn't care. He never cares. He only cares about shoving his painfully-hard cock into my tight virgin brown hole. He lies back on top of me, and we kiss again. I'm too intoxicated to stop it, nor do I really want to. I want him to relieve himself inside me. He slowly enters me, and I groan and whimper, but take him like a good girl. I don't want to disappoint him, like it's extremely important to me to please him.

He fucks me, slowly at first, but then harder and deeper. I'm too tight and unaccustomed to having a cock inside my ass, and so the experience is sort of mixed for me. Still, I don't hold him back. I let him use me, use my butthole, until he comes inside my bowels. He pulls out, and his plentiful jizz leaks from my sore little anus. Later on, he might fuck me from behind while I lie on my stomach. He's insatiable, and I'm super-raw, and yet, I can't say no to him. He needs to be satisfied.

All of my fantasies are in the vein of that one, but sometimes the guy brings on a friend. They take turns on me. While one thrusts into my ass, I pleasure the other with my mouth. Lately, double penetration has also crept up into my fantasies. One common denominator in all of my fantasies is that the guys never care about me or my cock. They don't blow me or anything. They just use me like a cum dumpster. They're also very masculine and dominating while I'm submissive, just a feminine little slut.

You're probably wondering why I just told you all of this. Well, if you read my opening sentence, you know where we're heading.

Because the divorce has pretty much left me broke, and because my day job isn't particularly lucrative, I had taken up cleaning houses a couple times a week to help pay the bills. It makes a lot of difference now that almost half of my salary goes to child support.

Anyway, there this gay man I clean for. He's in his early fifties and very much the gay stereotype. He's kind of feminine and unattractive, though I could definitely do worse. We're the same height and appear to be of the same weight. His hair is grayed out, though, and he wears spectacles.

The first time I cleaned for him, he was very nice to me, buying me lunch and making me coffee. I knew he would love to have sex with me, but I was still fighting myself. I mean, was I really going to have sex with a dude? I don't find even the best-looking men attractive, and I most definitely wasn't finding him appealing. Still, I had an itch that didn't want to go away.

The second time I cleaned for him was a month later. Again, he was super-nice and stuff, and I decided that if the opportunity arose, I would do it: I would have sex with a man. I finished cleaning his place after a few hours, and he suggested we'd have lunch together. I wasn't very hungry, but I agreed after he offered me a cool beer. Before I opened the beer, he asked me if I wanted to take a shower.

I knew where he was going with this, and so I... agreed. I took a shower while he set the table. I made sure I was clean for him, soaping my asshole several times, trying to stretch myself in the process. I was so tight, and it hurt sliding two soapy fingers up my butt. As hard as I tried I couldn't do it. We sat down for lunch minutes later, and I consumed three of his beers. Those were 10% alcohol each.

After we fed, we moved to his living room and just watched TV. I was fairly intoxicated already, and that third beer hadn't even started working. I knew I'd be hammered in like twenty. His sofa was L-shaped, and I was lying on the short end of it. He was sitting to my right, just next to my head that was resting against the pillows. I would brush my arm against his knee whenever I reached for my beer. I could tell it affected him, and minutes later, he started rubbing my arm, which was super-lame and just awkward, but I knew he was only testing the waters.

He kept massaging my arm when he saw I wasn't stopping him. I wasn't even looking at him. I was staring at the TV, but I was too drunk to really focus. Instead, I concentrated on that awkward massage while asking myself some tough questions:

"What the fuck am I doing? How the fuck did I get myself in this fucking situation? Why am I such a fucking underachiever? Where do I go from here? How can I start making some serious money because my life is so shitty at the moment? Why is this 'arm-massage' so fucking lame? Kinda grosses me out..."

While I was pondering all of this, he was growing more brazen, and after a while, he started stroking my collarbone under my shirt. While I found no answers to any of those questions, I was able to answer one query at least: I was going to have sex with him. I had to. He was all grabby and fuck, so hot for me now. I couldn't turn him down.

I called out his name. It was the first word either of us had said since he started touching me.

His hand froze on my collarbone. "Yeah?"

I could sense how tense he was. He knew I was straight, and I guess he didn't know how I was going to respond to all of this lame-ass fondling. Little did he know that today was his lucky day.

"Do you want to fuck me?" I asked plainly, staring blankly at the TV.

Even though I never looked at him, it wasn't because I felt ashamed. One does not feel ashamed when inebriated. I was simply bored, and he was going too slow for me. I was never going to allow this to be relegated to a pathetic make-out session.

"I'd love to," he replied in his sort of creepy sexy way as he reached for my groin.

I instantly rose to my feet, standing with my back to him, and pulled down my shorts and underwear.

"Okay," I could hear him murmur in disbelief as I walked straight into his gay bedroom which was just in front of me.

I lay down on his bed with only my shirt on, spread my legs and touched myself. He quickly joined me and started taking off his pants and underwear. He seemed impressed with the size of my flaccid penis because he kept commenting on it while he was getting undressed.

I really didn't understand what was so extraordinary about it. I have a six-inch cock, circumcised, girth on the slender size of average. It's nice a dick, but nothing to write home about. As he bared his cock to me, I understood his remarks. He was maybe a hair thicker than me, but at least an inch smaller. I knew I looked big next to him, and I couldn't fucking care less. I just wanted him to pop this straight dude's cherry already.

He climbed the bed on his knees and started stroking me, which felt nice, but definitely not mandatory. I was very drunk and very flaccid. Nothing about this was turning me on. However, I did find myself drifting into that feminine state I had mentioned earlier. It was challenging because he wasn't very manly at all, and his effeminate idiosyncrasies had really put me off, but I was determined to be a little slut. The alcohol certainly helped with that.

I started petting his hip while he was stroking my soft member. He seemed to love it, at first, but then he took my hand and put it on his dick. I flinched. Even though his cock was super-hard and right in front of my face, the thought of touching it hadn't even occurred to me until he made me do it. It unsettled me, holding a cock other than my own. I wanted to jerk my hand away.

But I didn't. I knew I flinched because I was drunk and he had just caught me by surprise. While he was working to get me hard in his hand, I gave it a few strokes. It felt weird. I didn't care much for it, but I wasn't feeling that burning need to let go anymore, either. Suddenly, it occurred to me that not only could I stroke it, but I could also suck it. I wanted to suck it, to have a hard cock in my mouth for the first time.

I took him in my mouth with a sort of zeal that truly surprised me. It felt... gross. I kinda wanted to vomit at the feeling of this taut penis in my mouth. This was nothing like eating a pussy. It was hard with a distinctive crown. I could feel the contours of the billowing head on my tongue, and it disgusted me. But he was loving it, sighing in pleasure. He clearly wanted his cock in my mouth, so I wasn't going to disappoint him.

I started sucking. It didn't feel all that gross anymore. I looked up at him as I was further settling into the female role of this interaction. His eyes were closed, and his face was full of excitement. It kinda annoyed me. Here I am sucking on your cock and staring up at you. The least you could do is reward me for that.

I really wanted him to look down to meet my eyes as this straight guy was sucking his cock, his first cock ever. I wanted him to put his hand around the back of my head and make me gag while I blew him like a little bitch. He didn't do any of that, sadly. He just pushed my pelvis back and lay down parallel to me so he could suck my dick, too.

That didn't jell with me at all. I was super-repulsed by the feeling of my cock in his mouth, but I soldered on, getting a nice sucking rhythm going. Soon, I was sucking him like a pro. I know it's hard to believe, but I was a much better cocksucker than he was. While he was simply bobbing his head on half of my dick and playing with my asshole, my head was rippling down his cock, almost all the way down. I took him out and licked up the shaft, licked his balls, before I sucked him into my mouth again.

He was shaved, while I wasn't. I was never into shaving, and I always preferred my women not to shave either. I'm a huge fan of the womanly bush. I was getting increasingly irritated by him sucking my cock. This wasn't supposed to go down like that. He shouldn't care about me, and I was all kinds of grossed out by it. I just wanted him to use me, that's it.

I took out his cock and made him stop blowing me. He asked if I was close. I would've laughed if it wasn't so sad. I told him I wanted him to fuck me already before I left the room to take a leak. I could feel my head spinning round and round. Normally, I'm able to consume large quantities of alcohol and not be terribly affected by it. Today, I was drinking on an empty stomach. I barely touched the food, and those beers were potent.

As I returned to the bedroom, I could see him tinkering with his stereo. It was kind of sweet that he even bothered. I lay back on his bed. Both of our shirts were still on. He took out the lube and extracted a glob of it. He stroked my again flaccid cock and put some of it on my anus, too. He then coated his dick. While he did, I asked if it would hurt.

I don't why I asked that since I knew how it would feel. Throughout the years, I would on occasion penetrate myself with my middle finger. I was always curious about it. Come to think of it, I had penetrated myself with a broomstick when I was eighteen. I had wrapped a nylon bag on the end of the stick and put plenty of soap. Shit, I guess those gay urges are rooted much deeper in me than I thought.

He was trying to give me an answer that wouldn't scare me away, but nothing was going to scare me away. Even if he was hung like a fucking horse, I would still take him, and take him all the way. That day, everything had come to a head. The stars aligned. He suggested that I should be on top. He said that would be the best position. I didn't want to be on top. I wanted him on top, doing me the way a man does his woman. He told me to raise my legs in the air, and I did.

That third beer had really kicked in by that time, and I was super-buzzed. I could feel the head of his circumcised cock probing my entrance, and it felt really good. It was all slippery and fuck, and I was very turned on by it. I knew he was going to bareback me, and I wouldn't have wanted it any other way. I would never ask him to put on a condom since I wanted to feel his cock flesh and was eager for him to come inside my ass.

I could feel him starting to push into me. It hurt. I was so fucking tight, and his mushroom felt huge. I winced, telling him to penetrate me slowly. I might've even called him baby. I think. I was hammered, and I really wanted to feel like a woman. He was patient, but it still hurt. I could feel my asshole stretching to its absolute limit.

Once I took the tip, I made him pause for a moment. I stroked his ass with my heels while I was getting used to his fat cock-head. He liked it when I stroked his ass like that, that I was being so feminine, and so did I. Most of all, I liked the fact that it pleased him. I then told him to push all the way in. My legs were high up in the air, and his arms were locked at either side of my head.

He shoved the rest of his hard cock into me, and I was surprised by how painless it was. He felt much smaller than he had a moment ago. I told him to hold still, so I could get used to him before he fucked me. Seconds later, he started moving inside me. I groaned, as this was both arousing and discomforting. I was definitely turned on as he fucked me tenderly.

He soon had a nice rhythm going, and he was really getting into it. He took off his shirt and pushed my legs back as far they would go. My knees were poking my shoulders, and even though I knew he was buried all the way inside my ass, I couldn't help feeling a bit disappointed that he wasn't bigger. I really wanted a bigger cock now that I was getting used to him.

"Is your cock all way in my ass?" I asked, just making sure.

He confirmed, fucking me thoughtfully.

Never mind. I was still very much enjoying his dick in my virgin bottom.

The longer we fucked to the hotter he was getting, as was I. He felt really good inside of me, and the whole position really turned me on, with my knees pulled all the way back, nudging my shoulders. My cock was hard and pointing straight up my abdomen. And then he had to ruin it for me when he kissed me.

He had managed to take me by surprise again. I could feel his tongue in my mouth, and I was repulsed by it despite the fact that I was drunk. Maybe if he was better-looking and more masculine I would like to be kissed, but he wasn't, and so I ended the kiss immediately. It was then when I flipped us over. I didn't want him to kiss me again, and I was eager to try out new positions.

He was all for it. Clearly, this was his favorite position. He held his cock straight, and I impaled myself on him. Again, the penetration hurt, and I groaned over and over as I fought to take him. I liked the fact that I was moaning. I felt like a woman, more than I had felt when he was on top. I could also feel his cock much better up my ass. This was perfect.

I rose and fell on him, slowly, tentatively, a couple of times, just making sure I was okay with the deeper penetration. I was still feeling a whole lot of discomfort, but also plenty of pleasure. He stroked my hard cock while I bobbed on him. I was soon feeling better with his size, and I began undulating, the way girls used to ride me.

He was surprised by my technique. His face beamed with excitement, and he even told me I was moving like a pro. It felt good knowing that, though I also knew I needed much more practice to really take it to the next level. Every time I pushed forward and up, my dick slid forth in his fist. When my ass swallowed him back in, my dick slid backward. I was lubed and hard, and it felt good, getting pleasure while I rode him.

I was really getting that feminine feeling I was chasing, undulating on top of him. I groaned repeatedly as his cock felt much more substantial and discomforting in this position, which I very much liked. I took off my shirt and pushed my palms into his chest, so I could move better, and soon I was super-feminine as I rode him, calling him baby and moaning, imploring him to come in my ass. Every time his cock slid out, I held it straight up and groaned like a slut as I impaled myself on him, and every time it hurt.