I'm Bisexual

I walked up the front stairs of my apartment porch, and peeked into the windows. The lights were off, meaning that most likely none of my roommates were home yet, so I opened the door and entered, and became a little less nervous.

I had just left a friend's birthday party, earlier than everyone else. I slipped out quietly while everyone was too drunk and excited to notice. My mind and body were humming, since I was still pretty buzzed myself. The party had been fun, but no different than any other. I could tell everyone was planning to stay out and celebrate for a lot longer. Normally I loved doing that too, but tonight was different. Whether it was the drinks or the culmination of thoughts I'd been having more and more recently, I was feeling incredibly horny.

Over the past year or so, I had found myself getting more curious about what it would be like to have sex with a guy. I didn't really consider myself bisexual (not yet, at least), but I noticed that as I watched porn I enjoyed imagining what it would be like to be in the girls' position -- to be on my knees worshiping a nice cock, or being pinned down on the bed and having my ass fucked.

It was the summer between my junior and senior years at college in Boston. I was staying in town to take some necessary summer classes, so I subletted a room at a friend's apartment in the Allston neighborhood. As I walked through the apartment I passed through kitchen and pulled myself a beer out of the fridge. I popped the tab on the can, paused, and looked and listened one last time for any noise. All the bedroom lights were out -- no one was home, or if they were, they were already passed out for the night. I didn't want any of my roommates to find out what I was doing -- it was awkward enough figuring out my sexuality on my own. I walked into my room, and turned on my laptop as I took a nervous sip of beer. I had finally convinced myself to give this a try, and I didn't want to lose my courage.

Soon I had Craigslist personals up on the screen. This was something I'd done many times before, but usually I just read some m4m ads, fantasized about answering them, and masturbated before falling asleep. Tonight I was determined to follow through, to at least try to find someone patient and fun to explore with. I replied to a couple of ads for guys that seemed to live nearby, but I either got no response back, or really creepy, aggressive, off-putting ones. I wanted to hook up, but I wanted to feel the guy out first, and not just blindly meet up with a creep.

After a while, I was about to give up on the night, when I noticed a reply had come in from one of the first ads I responded to that night. The guy had written an ad describing himself as a bisexual guy in his early 30's, a who was a bit stocky. He was just what I was looking for, since I found myself fantasizing most often about older, heavier guys. I certainly wasn't an athlete or a model myself, being a few extra pounds above average. In my original email to him I had described my curiosity, and how I was eager to lose my virginity to a guy like him.

His reply read,

hey dude, nice stats and pics! i'm jim. i'm def interested in playing tonight if u still are. u being a virgin is not a problem, i'd love to help teach you the ropes. like i said in my ad i'm looking to top for a guy like u. i'm patient and we don't have to do anything u don't want to do. ive attached my pics too. let me know ;)

Jim definitely sounded like the type of guy I fantasized about. I replied with a few more pictures of myself that I took from my laptop, and tried my best to flirt about how excited I was to meet up. I told him I needed to travel to him, since I lived with roommates and I didn't know when they would be home. His original ad said that he lived in the same general neighborhood as me, but as we talked it turned out that his apartment was only two blocks away from mine. It was as good a sign as any that this was the night I was meant to give in to my curiosity. After some nervous hesitation, I replied that I would meet him at his apartment in about half an hour.

I chugged the remainder of my beer, and hopped in the shower to freshen up. As the water flowed over me, I took some time to trim my pubic area, and shave around my asshole. I wanted to make sure I felt sexy for my first time. While rinsing, my hand worked its way to my ass, and I fingered myself for a minute in excitement.

After drying myself off, I threw on a loose t-shirt and some basketball shorts with no underwear underneath. I could smell the shampoo drying with my hair, and I smelled fresh. Still riding my buzz, I took a deep breath, opened up the front door, and walked out into the cool night.

Even though Jim's apartment was only a short walk away, I was nervous and excited, so it seemed like it took an eternity to get there. I could feel adrenaline pulsing through me as I walked beneath the calmly rustling trees. When I arrived at his place, I was surprised to notice that the building was one of the red brick town houses that I passed by almost everyday on my way to class. He said he was on the first floor, in the first apartment to the right. After hesitating at the door for a moment, I took a deep breath and rung the bell to his unit. It couldn't have been a long time between me ringing and him answering, but at the time it seemed like an eternity. What am I doing? If there was any time to turn around this was it. But my horniness won out.

Soon front door latch buzzed, and the door unlocked. I walked into the harsh fluorescent-lit hallway, and saw the door to my right unlock and hinge open just a crack. I walked up to the door, and gave it a little tap as I pushed it open. On the other side was Jim, silhouetted by a lamp behind him in an otherwise dark living room. He was just as he described himself—about 10 years older, with a little bit of a belly, shaved bald head, and a stubbly, attractive face.

"Hi," he said. "You're cute."

Jim took my hand, led me inside the apartment, and closed the door behind me, locking it with a click. He started to gently run his hands over my chest, and then around my body, working his way to my ass, giving it a little squeeze. Then he leaned in towards me, brushed his lips against mine, and pulled me into a deep kiss. I had never kissed a man before, but it felt surprisingly natural, even in my nervous excitement. He pressed his lips to mine with a forceful masculinity, his tongue pushing its way into my mouth. I relaxed my lips and kissed him back, finding myself turned on by the rough feeling of his stubble against my face.

After a few minutes of making out just a step inside the front door of his apartment, I pulled back, sucking on his bottom lip.

"Thanks," I said. "So are you."

Jim's eyes gleamed, and he leaned back in to kiss me again, gently pushing me against the back of the front door. We didn't talk much -- and I'm kinda glad, because it let me lose myself in the sensations instead of giving me a chance to have any second thoughts.

We broke the kiss again. He looked me up and down in the dim light, then slid his hand on my ass and guided me toward the bedroom with it. Just feeling his strong hands on my body made me tingle as we walked down the short hallway to his darkened bedroom. Once there he lifted my t-shirt up as I shimmied my shorts down my legs, leaving me fully naked. Jim removed his clothes as well, and once he was out of his clothes my eyes were drawn to his rock-hard cock. It was about 7 inches long, with a nice thickness to it. He pulled my body into his and we dove back into another deep kiss. I rubbed my hands over his chest as he massaged my ass, digging his hands into me and pulling me close, our cocks grinding together.

We kissed with our bodies close for a few minutes, each moment of contact between our hard cocks sending sparks though my body. Jim pulled away, and stepped backwards toward his bed. He sat on the edge of the mattress and stroked his cock slowly. I couldn't take my eyes off of it.

"You said you wanted to try sucking cock?" he said as he leaned backwards, his shaved cock standing straight up into the air. Without even thinking about it, I had already dropped to my knees. I crawled over to the bed, kneeling in between Jim's legs, and took his throbbing cock in my hand. Touching another man's cock was different than I expected. It was warm, and softer on the outside than I had imagined, while being very hard at the same time. It was so different and more electrifying than just touching my own. After stroking him for a moment, I brought my mouth up to it, and gave the tip a soft, gentle lick.

Jim uttered a slight moan when my tongue touched him, so I did it again, this time holding my lips there before sliding my tongue all the way down the underside of his cock, down to his balls. I licked around them and sucked them gently, enjoying the feeling of them moving around in my mouth. I was encouraged by the moans they elicited from Jim. Then I licked my way back up his shaft; I was surprised at how much I loved the feeling of his warm cock against my tongue and lips. After exploring his dick from top to bottom, I moved my mouth back to the tip of his cock and slowly started sucking in, tightening my lips around his cock. Looking up, I saw him close his eyes in pleasure and let out another moan -- I knew I couldn't have been doing too bad!

This encouraged me, and I started sucking him in earnest. I wrapped my lips around him and bobbed my head up and down, swirling my tongue around his shaft as I sucked him as deep as I could. I felt the thickness of his cock filling my mouth and hitting the back of my throat. He moaned a bit louder. I started caressing his balls with my hand, while I built up a rhythm with my mouth. Licking the head of his cock, taking him until my lips reached the base of his dick, and pulling back. As I closed my lips around the tip of his cock, kissing it, I pulled back a string of salty precum, and licked it up.

Immediately I wrapped my lips around his thick cock again, working myself up and down. His moaning got louder and more frequent. He worked his fingers thorugh my hair, applying pressure to the back of my head, guiding my mouth, and pushing my lips down his cock, then up again. After a few minutes of me on my knees in front of him he put his palm on my forehead, and motioned for me to join him up on the bed. I climbed up next to him, making sure to get right back to work on his cock.

"Fuck, dude, you're doing great. Keep sucking," he said, closing his eyes and sighing, as he pulled my body around so that my ass faced him.

I kept my mouth on his dick, losing myself in the pleasure of having his hard dick between my lips, while I swiveled my hips to give him access to my ass. As I pulled my head back, and started licking up and down his cock, I could feel a bit of pressure at my ass. It was the tip of his finger, circling my virgin hole, teasing me. My surprised moan was muffled as I dove back down on his cock, sucking quickly and noisily, excited to have him fill my mouth.

He worked a finger inside of me while I sucked, slowly pushing in to his knuckle. I had never had anything beside my own finger in me before. It was a different sensation, having someone else do it. I let out an eager moan around his cock as I continued to suck him. In no time he was working another finger in. My ass felt slippery and a little bit cold as he did it -- he was applying lube while he stretched me. As he spread my ass and fingered me, I tried to deep throat him and take him as much as I could, bringing my lips down to the base of his dick. Each time, he gave a satisfied grunt, and stroked the inside of my ass with his fingers, sending shivers down my body each time the new sensation hit.

After a few minutes of this, he placed his free hand on my shoulder and slowly guided my mouth off of his cock.

"Damn, you were excited to do this," he said. "Lie face-down on the bed, I want to fuck your virgin ass so badly."

I obediently slid over on the bed to lay down in the center, face down. I felt the bed spring up and down a bit as he crawled up onto it with me. He reached down and spread my ass again, applying a little bit more lube with his index and middle finger. Behind me, I heard a ripping noise, followed by some wrinkly sounds. He was unwrapping and putting on a condom, and lubing it up. The bed bounced a bit again as he moved closer to me. I could feel the warmth of his body as his legs straddled me, and then he reached down, spread my cheeks, and placed the tip of his cock against my hole. His cock was warm, and felt much bigger against my ass than it had earlier.

I felt his hands on my hips as he balanced himself, then all of a sudden there was pressure at my hole. The pressure continued until I felt it give. Jim gave a deep involuntary moan, and so did I, as I felt a new sensation of fullness in my ass.

He sensed my anxiety, and said "Relax, just push out and relax. Gotta just adjust to it."

"You're good," I said, relaxing and willing myself to open up and take him.

"Almost there" he sighed.

He pushed slowly, filling me, until I felt his balls and body against my ass. I had never felt so full before, and even though it hurt a bit, I loved the feeling of his hard dick in my ass, stretching me. It was warm, and sent shiver up my body.

With a grunt, he pulled back, and then pushed back in again slowly, only slightly faster than last time, making sure my body adjusted to him. He did this for a while, building up a deep slow friction as he rhythmically pulled out and pushed back in. A feeling of fullness washed over me, and I tried to squeeze my ass around his cock like I had read about. He leaned forward, resting his hands on my hips and pushing down on my lower back to raise up my ass. He pounded me rhythmically, while I felt my hard cock straining beneath me against the bed, rubbing back and forth.

I still felt buzzed from my night out at the party earlier. This let me relax and melt into the bed as he continued to fuck my ass. With each thrust I heard a meaty slap and the slick sound of his cock sliding in and out of my lubed hole. He continued pounding my ass, grunting with each thrust, and I moaned as it started feeling more and more pleasurable.

I lost track of time as I got fucked like this, feeling sexy -- while everything was a bit surreal to be fulfilling something I'd been fantasizing and curious about. After quite a while of getting fucked on my stomach, he slowed down and pulled out of my ass. I felt his hand on my legs, then all of a sudden he has flipped me over, and I was on my back. He crawled up onto the bed with me, and kissed me deeply. We made out for a minute or two, and then he centered himself above me, holding himself up with his arms. He pushed into me, spreading my legs open and back against me, until his cock was at my hole again. He leaned down, kissed me, and pushed forward with a pleased grunt.

My legs opened more as he leaned into me, pushing his cock back inside my ass. I looked up at his stocky torso above me, watching his arms tense as he thrusted, his hips pumping into me over and over. His balls slapped against my ass as he lost himself, closed his eyes, and pounded me in this new position. I felt his cock stretching my ass, pushing it out in every direction. He panted and moaned, leaning down to give me a peck on the lips every few moments.

He leaned down a bit lower, flexing his arms. I brought my lips up to meet him, grabbing his bottom lip with both of mine, sucking it, then giving in to his deep kiss. I tightened my legs around his ass, trying to pull him close to me. He continued to pump into my ass, grunting masculinely as he adjusted his weight. He moved his hands to my nipples briefly, playing with them, sending sparks through my body. Then his hands continued down to my hips, where they held me to the bed as he continued his assault on my virgin hole.

I saw the sweat beading on his forehead, and the muscles in his arms flexing as he pounded me. He leaned down to kiss me, drove his tongue between my lips, then pulled back, pulling his cock out too. He gave me another quick peck, then grabbed my ankles with each hand, pulling my legs so that they were resting on his shoulders.

"Fuck, get back inside me," I moan.

He smiled, grunted, and lined up his cock against my hole, leaning back against me and filling me once again.

"Mmmm I love fucking your virgin hole," he sighed, as he bottomed out against me. Then he continued his assault. He leaned forward more and more as he fucked me, till my legs were pinned against my chest. I felt him driving deeper and deeper, panting harder, as he appeared to get closer to cumming. He leaned down, kissed me again, then pulled back and started to shout that he's coming. I used my legs to pull him into me, moaning and screaming to fuck me, that I wanted his cum.

He cums, and shudders, and falls down against me. We're both panting, grinning, and give ourselves a moment. Then he slowly slides out of my ass.

He stands up at the edge of the bed, sweat dripping all over his body. Looking sexy. My ass feels empty, and a certain sort of shame comes over me. I realize how late it is, that I'm laying in a stranger's bed after just having sex with another guy. That overall, I liked it, but it's a new feeling.

Jim walks over to his living room, and I follow. My clothes are on the ground. He sits down naked at the couch, and starts messing around on his laptop. He smiles at me, and says, "Damn, dude, you wore me out!" We exchange numbers. I sit naked next to him for a second, then realizing how late it is, I tell him it was fun, get up, and leave.

As I walk through the windy night the two blocks back to my apartment, I'm glowing, feeling sexy and electric, my ass loose and tingling, and I can't wait to do something like this again.