First Time

This is my first submission after over ten years of reading some truly erotic and orgasm inducing stories. As any virgin will say, please be gentle on me ;)

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My name is Scotty Valentine, and here is my first gay experience.

My realization that I am bisexual came in my early twenties. I had masturbated as a teenager about what it would feel like to hold another cock in my hands, but never took it further than that. Then Internet porn allowed me my first glimpse on the sheer sexuality that is experienced with same sex coupling. I would admire the lesbian videos, but then made my way to guy on guy. My cock never got as big as watching two big uncut guys 69 each other. Then came the Craigslist prowling. Seeing what men were out there that wanted to indulge in some no strings attached fun. I browsed until I found an ad that peeked my interest. "Male with panty fetish seeking top", was the headline. He was an Asian panty boy, who loved to wear panties just before he was fucked. We arranged to meet that night at his place, which was not far from where I lived.

I was nervous to say the least. I had always fantasized about fucking a man, but could I go through with it? When I saw another cock for the first time, would I want to suck it, or would I run away in terror? I took a nice long shower, making sure to shave my balls of all hair till I was nice and smooth. I rubbed some lotion on to avoid irritation. My 7 inch, uncut cock was swelling with anticipation. I smoked a bowl, took a shot and headed out the door into the night.

I remember the walk to the train and the trip there as one of the longest, most anticipated trips I ever took. Before I knew it, I was at his front door. I texted him to let him know I was out front and the bell buzzed to let me in. His door was the first door in the building, and I nervously knocked on the door. He opened the door with a big smile. He was just shorter than me at around 6'1, he weighed about 160, slender with short black hair. He was wearing a dark pair of loose sweat pants and a white t-shirt.

"So you're Scotty," he said. "I'm Kenny, and you look every bit delicious as your photo".

"Thanks," I said nervously with a laugh. "You, um, look good too."

"Aw, thank you sweetie!" He cooed. "Please come in, I know it's cold out!"

I walked into a neat and clean living room. There was a nice Christmas tree up, and the TV was playing Christmas cartoons.

"Nice tree," I commented, trying to break the ice and play it cool while being polite.

"Thanks, baby. I try to keep things festive around the holidays. Why don't you give me your coat and you can sit down," Kenny said, as he took my coat and put it on a coat rack by the door. "Would you like some wine? It will help you relax"

I nodded graciously with a smile and say down and looked around. I realized my cock was raging hard and leaking pre cum like a broken water main. I could feel my damp boxers and felt slightly embarrassed. That's when Kenny returned with two glasses of white which he handed to me with a smile and a wink. He sat on the same couch as me, just one space away.

He was quiet as he sipped his wined and seductively looked me up and down. He bit his lip and looked into my eyes, and I felt my cock pulse with excitement.

"So is this really your first time, Scotty," Kenny asked with a smile. "I don't mind if it is, I'm just curious."

"It really is," I said with a smile. "I'm a little nervous, in case you can't tell".

"Oh I can tell baby, and I think it's sexy as hell."

He was quiet after that as he took a big gulp of his wine. I followed suit and downed three quarters of the glass while staring him in the eye. That's when I looked down and saw the tent building in his pants. My own cock jumped knowing he was just as arroused as I was.

"Does it bother you that I have women's panties on," Kenny asked. " I loved the silk feeling against my hard cock."

"I don't mind at all," I said, as I reached down and re-adjusted my erection.

"Let's take this into my room," Kenny said, as he stood and took my wine glass and put his and mine on the coffee table. He then reached down, took my hand and lead me to his bedroom. As we walked with my hand locked into his, his other hand untied his sweat pants and let them drop, revealing a pair of slightly hairy, slender legs, that ended in a red pair of self boy shorts. I admired Lenny's bubble shaped ass as he lead me to my first experience.

We stepped into a room that was lit a lamp that had a red bulb, bathing the room in a dark red light. The bed was a full size and stood in the center. Just before I could look around, Kenny turned and leaned in and kissed me full on the mouth. We instantly melted into each others lips, opening our mouths and exploring each other with our tongues. I could feel his hard cock through his panties, poking me in the stomach. I reached down and rubbed his head through the fabric, causing him to moan. He stopped me though and raided my hands away.

"Me first sexy," he said with a grin. "I want you to really enjoy your first time."

He pulled my shirt over my head and I quickly allowed him to make me shirtless. He slowly unbuckled my jeans and lowered them revealing my tented boxers, with a dark wet spot on the front.

"Oh my!" Kenny exclaimed with delight, "someone is really horny for me. He pulled my boxers over my stiff cock, and revealed my 7 in cock, the hood pulled all the way off the head and completely glistening with pre cum. "Look at this juicy treat you have for me!"

With one gulp, he engulfs my entire cock down his throat, slowly pulling back and sucking the pre cum all off my cock head and making a slurping pop as he takes me out of his mouth. It's a good thing he does because I feel like I'm ready to bust.

"Lay down on your stomach," Kenny instructs me, " I'm going to give you a nice back rub, so you can fuck me nice and deep afterwards and not strain your back" he finishes with a wink.

I crawl on his bed, as I feel him pull my pants and boxers completely off my legs, and manages to pull my socks off too, leaving me completely naked. I then lay face down in the center and turn my head to the side. I feel him crawl on top of me, and suddenly feel his hard cock rest between my ass cheeks, spreading them slightly, as he leans forward and starts rubbing the tension out of my shoulders. I instantly moan approval, feeling his strong hands rub the tension out of my muscles in my shoulders, then down between my shoulder blades, down to the muscles in my lower back. But the real pleasure is feeling another man's erect penis in such a compromising position. He was literally an inch from sliding his cock into my ass. The idea of this was nerve wrecking because I didn't think I was ready for that, but still was the best message I ever had.

"How does it feel baby," Kenny asked as he continued to rub all the tension out of my muscles.

"Mmmmm, feels absolutely amazing" I said with absolute sincerity.

"Does it turn you on that its a man doing this to you," Kenny asked as he slid his cock up and down my crack. "Do you want me to suck your cock Scotty? Do you want to fuck me till you cum deep inside me?"

All I could do was moan loudly. He lifted himself off me and quickly turned me onto my back, my erection sticking straight up to the ceiling. He began to suck me off slowly. Teasing my cock head with his tongue. He was laying in a position where his cock was within my reach. I stretched out and took it in my hand. Admiring the soft hot feeling it had. He has circumsized, unlike me and it was erotic seeing a completely different cock up close. He also did not shave and had a full bush, that I found sexy as hell. He had a musty, yet soapy smell to his crotch as I tried to reach further down.

"Do you want to suck my cock too baby" Kenny asked as he removed my cock from his mouth. I quickly nodded and he maneuvered himself so we lay in a sideways 69. I quickly engulfed my mouth over his cock. At this point I was a horny mess and I wanted it all. I played with his hairy balls as I greedy sucked his cock, at the same time enjoying the job he was doing on me. I grasped his ass cheeks as he began to fuck my mouth with his hard cock, tickling my nose with his pubic hair. I slipped two fingers into his tight ass and started to fuck his ass as he fucked my throat, working up a great rhythm. I became so horny that he could have fucked me right there. That was when my fingers hit his gspot, causing him to shoot rope after rope of cum down my throat. I gaged a little at first, but quickly swallowed every drop. Panting he pulled himself off my cock and layer on his back. His dick still pulsing from the orgasm he had.

"Oh my god baby," he panted, "are you sure your a virgin? Because no virgin has ever made me cum from sucking my cock before!"

I couldn't help but smile at the compliment. "Beginners luck, I suppose," I said with a goofy smile, and stroked cock.

"Well just for that, I think you earned a special way for your first time," Kenny said as he stood and walked over to his dresser. He came back and was holding a bottle of baby oil. He tossed it to me. "First, you have to get my ass wet baby, while I get your cock ready."

Kenny then laid me on my back, and walked around the bed to stand over my head. He then took the bottle of baby oil from my hands and climbed on top of me, straddling my face and lowering his tight ass over my mouth. I reach up and pull his ass apart exposing his tight little asshole. I start to lick and shoving my tongue through the sphincter. I hear him moan as I hear him open the oil bottle and feel the warm oil trickle on my cock, and feel him stroke me, while getting me well lubed. I continue to tongue fuck his tight hole, savoring his musty, taste. I slip a finger in, then two, then three, pulling out and licking.

Suddenly he stands up and lays next to me on his back, facing me. "It's time to fuck me baby," he says with lust in his eyes.

"What about a condom," I ask, already regretting it.

"Normally I'd already have you in one. But you let me cum in your mouth, and you swallowed. I think that your first time should be bareback, and you should feel your cum shoot in me."

I'm so horny, I instantly crawl on top of him as he spreads his legs. I reach down and grasp my oiled member and guide it to his tight ass and push past his sphincter and sink all the way in till my balls are resting on his ass. Kenny locks his legs around me as I stop and enjoy my first time in a mans tight ass. It's so much more tighter and hotter than any pussy on the planet. I begin to make out with Kenny, as I slide out just before my head comes out, and instantly slam back in. I build up a good rhythm our pelvises mashing together. I feel his hard cock sliding between our bellies, and feel his pre cum leaking as I brush up against his prostate with each thrust. My then grab on to his slick cock and start to pump it as I build up more speed.

I feel my balls begin to boil and know that I'm close to blasting into Kenny with a tidal wave.

"Oh, Kenny, I'm going to cum!!"

"That's it baby, cum for me!! Cum inside me!! Make me your bitch baby!!"

That's all I need to hear, as I unleash several ropes of cum deep in Kenny's ass. I am exhausted and collapse on top of him. Kissing him deeply as we feel my cock slip out of his ass.

That was only the first hour I was there. If there is any interest. I will share the rest.