My First Gay Experience

I'm in my mid-30s and definitely attracted to women. However, there is something about guys and gay porn that turn me on. Some of my best jerk-off sessions involved fantasizing about having a gay encounter. Over the years, I've explored playing with my ass. I started with sticking a finger up my asshole but that didn't do much for me. So I started experimenting with inserting different phallic-shaped objects. I started small but craved trying longer and thicker ones. Watching porn while jerking off with one hand and fucking my ass with the other was a hot experience. But I wanted to feel the real thing inside of me and began browsing gay dating sites. The thought of it made me horny but I didn't have the courage to pull through on my fantasy. Recently, I stumbled onto the profile of an older guy in his 50s who said he liked fucking younger guys and was available to meet up for the weekend. After the typical hesitation, I finally caved and couldn't wait for my first gay experience.

My heart was racing on the way to the motel. Am I really going to go through with this? There's still time to back out if I want. But I can't let this opportunity slip away now. So I finally arrive at the motel room where we are supposed to meet and knock at the door. He tells me to come in and lock the door. I finally get to meet the guy I'm about to have sex with and my heart begins racing even harder. This guy is indeed older with greying hair and a little beard. He remains seated and introduces himself as Rob.

"Hi, it's great to meet you. This is my first time with a guy so please take it easy. And...uhm...I brought some condoms and lube in case you don't have any," I explain.

"Sorry, I don't use condoms. I want to feel skin on skin. And I'll fuck you however I want, even if you find it painful," Rob replies.

I wanted my first time to be with a more experienced guy but this response shocked me. Red flags are going off and under normal circumstances I would back off. But I'm too horny now and if anything this made me even hornier.

He tells me to strip for him and I'm happy to oblige. I move over closer to him and begin swaying my hips. As I'm doing that, I begin unbuttoning my shirt and throw it down onto the floor. Next, I kick my shoes aside and turn around. I pull my jeans down and bend over to give Rob a good view of my ass. Now I'm just down to my undershirt and boxers that are having trouble containing my raging hard-on. Rob must be enjoying the strip tease as he had begun rubbing his dick through his pants. I turn back towards him and slowly take off the undershirt. Then I take a step towards Rob so I'm right in front of him and begin rubbing my dick through the boxers. He starts rubbing his dick even faster in response and leans forward with his mouth open.

I demand, "Stay right where you are and don't move another inch. Okay?" Rob seems like the type of guy who doesn't like to receive orders but I give him a naughty look and he acknowledges my request with a nod. I hold my penis with one hand and take off the boxers with the other hand. Rob was looking around with his eyes to get a peek of my dick but I made sure to have it not be visible to him. I want to prolong the teasing as much as possible for both of us. To that end, I place my boxers on his head so his eyes are covered and the crotch area goes down to his nose so he can smell it. I release the hold on my dick and start jerking off a mere inch away from him. Rob can't take the teasing any longer and throws my boxers to the side while licking his lips in excitement.

A mere moment later, Rob engulfs my entire shaft into his mouth. I can't believe it; it's my first time getting head from a guy and he's jumping straight into deepthroating me. What a sight to behold and feeling to remember! He's bobbing his head up and down and tickling my balls with his facial hair. After a while of doing that, Rob pulls out and looks up at me with his lust-filled eyes. This encounter has been so hot thus far and even better than I could have imagined. He uses the brief rest to unzip his pants and whip out his own hard cock before turning his attention back onto mine. This time, Rob jerks me off with one hand while licking around my shaft. I was too excited that I didn't notice his other hand creeping towards my butt. Just like that, he inserts a finger into my asshole and begins moving in and out while continuing to give me oral sex.

"Fuck, that feels so good," I say. The pleasure and sensations are too much for me and I mention that I'm about to cum. Rob puts my dick into his mouth again and speeds up the finger-fucking of my asshole. I moan out loud and just as I begin to cum, he inserts a second finger into my widening asshole. Rob eagerly eats up all my cum as I ejaculate in several spurts.

That was amazing but there's not much time to reflect. Rob finally gets up and pushes me onto the bed. He pulls my legs up in the air so my ass is fully exposed. He kneels down briefly to lick in and around my pink hole before getting back up. Next, he spits a couple times on his dick to coat it with his saliva and moves it close to my butt. This is it! This is what I've been fantasizing about to feel a real, hard, manly cock inside of me. A nervous excitement comes over me as I feel his tip pressing against my anus. Rob tries pushing it in but I flinch. I regain my composure and relax myself and my anus. Rob tries again and this time he's able to penetrate me. I can't believe the sensation as more and more of his cock enters me and stretches out my innards. He must have finally reached the end as he stops for a second and looks down at me.

"You're so fucking tight. Are you enjoying it as much as I am," asks Rob. I smile and nod just as he starts pulling back out.

This is crazy. I'm having rough unprotected gay sex with a total stranger but I'm loving every second of it. Rob picks up the pace and starts thrusting in and out faster. I scream out loud from a mix of pain and pleasure. His makeshift saliva lube had worn off by now but I don't care as I want him to keep going and enjoy my tight hole. "Fuck me harder" I proclaim against logic but instead Rob stops and pulls out completely. Before I can process what's going on, he puts my legs down and straddles me. With his dick mere inches away from my mouth, I know what he's looking for. This is going to be my first time sucking another man's cock. Not only that, but I'm about to have my first ass-to-mouth experience. The thought had crossed my mind before but I never went through with it while playing with my own ass. But now I decide to go for it and begin licking his manhood like a cock-hungry slut. After doing this for a while, I put his dick into my mouth. There's only so much of it I can take due to my inexperience. My head motion is also limited from being pinned down on the bed. So Rob takes action and pushes his dick deeper into my mouth. I feel like I'm going to choke and I start gagging but he doesn't let up. Instead of fighting back, I learn to deal with this new sensation and let him have his way. Rob pushes more of his dick into my mouth and I just focus on keeping it as wide open for him as I can.

After he had his fun with my mouth, Rob pulls out and turns me over so I'm on all fours on the bed in 'doggie' position. He slaps my ass cheeks playfully, sending a shiver down my body. I try my best to present him an inviting opening by pushing out and gaping my asshole. Without warning, Rob shoves his whole dick up my ass in one go. Fuck! Once again, it hurts so good having another man's cock up my ass without lube. At least some of my saliva was still on his dick. Rob grabs me by the waist and starts fucking me in earnest. It feels great getting my ass stuffed from this position but I want more.

"C'mon, you can go faster than that. Fuck me harder," I request. Rob goes for it and thrusts in and out as fast as he can. We both moan hard and yell out expletives. Getting fucked like this by a real dick feels amazing; I don't want this experience to end. It's even better knowing that I'm also giving pleasure to another man. As I'm enjoying the moment, I notice Rob slowing down and feel something else inside of me. He is cumming inside of me! Once he finished, we both collapse on the bed from exhaustion. As I start feeling some of the cum dripping out of me, I scoop it up and swallow it. I'm not going to be denied tasting another man's cum for the first time.