My first steps into the bisexual life, with an anonymous man
What a crappy New Years this had turned out to be. Stuck in a city where I knew basically no one, away from family and the long-term friends, I had stayed in and watched reruns of House instead of getting out and trying to find something exciting to do. When New Years itself had dawned, gray and with a slight chill in the air, I wandered around my small apartment waiting for something to strike me as interesting. The day wore on, and I hopped online to check my accounts, see if anyone on the meet-up groups had messaged me, when I got the urge.
I had been getting the urge for a long time. I had always been a regular pornography watcher, but in recent months my tastes had shifted. I still watched the usual man on woman porn, the hard fucks, barely legal teens, and group sex scenes, but I had started to drift into new territory. Two men with a girl, but the men were often more interested in each other than her, she was just to help occupy the cock left out. Interracial play where the big black cock was dipping into a man's ass rather than a tight pussy. I had even purchased several toys, using them on myself while watching this new eroticism play out in front of me.
Porn, and some online anonymous chatting, was as far as it had ever gone. I felt my urge build up, and played with myself until I was gratified, and then it subsided. Sometimes for months, but recently it had been only days that had gone by until I wanted to shove that purple silicone cock back up my ass, letting it rub against my prostate until I came hard in the oversized chair at my computer. I wasn't completely sure how I felt about it, but it didn't matter, I was alone, and horny, and wanted it. Today was no different, so I chatted with several different people, making up wild stories together as I sat there naked, when one of my accounts chimed.
"Hey, like ur pics," was all it said. I noticed the user, Bearboi67, was online, so I shot him a message back, "Thanks, can't see yours since I'm a basic member. Want to chat?" And in an instant an IM popped up.
This thrill was different. No longer was it some anonymous male (if they were even males, who knows), but someone who had seen pictures of my own body, my toys, my cock in my hands. And he lived in the same city as me. We chatted slowly, him trying to tease out what I had and had not done, me being very honest with him. I was basically a bisexual virgin, plenty of women in the past, but no men. He said that was too bad, inquiring what I might want to try if I had a man in front of me. Finally, he led the way with, "so, you want to meet?"
I sat there wondering what to say in response. I had thought about this before, whether to say yes or not, how it might go. Finally, in a moment of brazen adventure, I type, "sure. where and when?" He directed me to a local bar that would be quiet, and in 2 hours I was standing in front of it, pushing the door that would change my life forever. He was sitting to one side of the bar, with a few other people strewn about, chatting quietly. He was a large man, overweight, with short read hair and goatee. I sat next to Alan and we chatted, drinking a few. He could tell my tension and apprehension, and seemed ok with taking it slow. When he asked did I want to come back with him, I agreed, less nervous now.
I followed him back to his house, where we continued to drink some, and 2 bottles of wine later I was flying loose. He took me upstairs, undressing on the way, and he slipped into bed naked and then asked me to undress in front of him. I started slowly, unbuttoning my shirt, showing my fairly muscular chest, with a little extra padding on the sides. He encouraged me and I slipped the belt from my waist, and as I started to unzip my pants he pulled the covers back, showing off his hard cock as he was stroking it. Now I was just as naked as he was, my own cock not as thick, but just as hard, and he had me crawl onto the bed, slowly getting to him where he wanted to kiss me. I refused, saying I wasn't ready for that, so instead he pointed me down to his cock, and asked if I wanted to try him. I gulped, but nodded, and maneuvered down between his legs, wrapping my fingers around his thick hardon. I lowered my head, and letting my tongue stick out I dragged my tongue across his cockhead, tasting for the first time another man. Alan moaned appreciatively, and quietly directed me to lick more. I copied what I had seen in the movies, eager to please him, and moved my tongue in small swirls around the tip of his cock, tasting the precum that was welling up from his shaft. Finally, I opened my mouth wider, and let him slide into me. His large hips moved up to greet my mouth, eagerly wanting to be in my mouth, and I felt his thick fleshy cock push past my lips and rest on my tongue. I couldn't fit all of him inside me, so I started to work up and down, my cheeks bowed inwards from how intensely I sucked him. My free hand was on the base of his cock, holding it firmly as I went to town on him, and I felt his cock quivering as my tongue slid down the thick vein on the underside, then back up to the head. I continued to blow him for what seemed like forever, his hands on the back of my head, playing with my hair, encouraging me, urging me on. I slowly got more of his cock into me when he announced he was ready to cum. He wanted to warn me, and asked if I wanted him to cum in my mouth, or elsewhere. I ignored him and kept bobbing, knowing that I had committed to this and was going to see it through. Besides, my own cock was dripping onto the sheets from how turned on I was. He grabbed my head and forced as much of his cock into me as he could, making me gag slightly, as he erupted into my mouth. I had never had the experience of a man cumming down my throat before, I had only done it to other women, and it was surprisingly hot and erotic. He pulled back, letting some of the cum reach my tongue and mouth, and I sucked it down, slurping the hot sticky cum from his shaft. I finally pulled off of him, rolling onto the bed beside him, as he lay there panting.
"That, that was your first time?" He gasped, and I nodded. "You're quite the natural cocksucker, aren't you?" He rolled onto his side, his fingers tracing along my chest and stomach, making my cock quiver even more. "What else can you do?" he wondered aloud, as he stood up and walked to his dresser. Opening the top drawer, he returned with a large dildo and tube of lube. "If you want to, roll over, and let's play some more."
By this time, the wine and the arousal had gotten the best of me, and all my inhibitions had flown right out the window. I rolled onto all 4s, practically wiggling my butt in his face as he laughed, crawling onto the bed. I felt the cold squirt of lube on my asscrack, his fingers massaging it between my ass cheeks slowly, and I lowered my head and tried to relax. The dildo he had was larger than mine, but the lube and the excitement and the wine conspired to let it slide into my virgin ass pretty easily. The silicone head pushing into my ass, I tensed a bit but sighed contentedly, much to Alan's delight. He reached under with his other hand and started to jerk me off, keeping the dildo moving in and out of my butt at the same time. My hips started to sway, moving back as he pushed the dildo into me, his hand slipping over my own shaft, working it furiously. With no warning he pulled the dildo from my ass, making a pop sound and surprising me. Then I felt him move behind me.
He lifted his big belly, allowing him to maneuver his cock towards my gaping asshole. I froze, not daring to think what was about to happen, a small bit of me still unsure this was what I wanted. Alan took that decision away from me as I felt the head of his cock nudging inside my asshole. I tried to relax, pushing back slightly, and with a thrust he was inside me, his head stretching my ass more than the dildo had. It hurt at first, a burning from the skin being stretched wide, and I gasped. But Alan was into fucking his little virgin now, and he hungrily pushed his cock deeper into my ass, until his belly prevented him from completely bottoming out inside of me. Still, at least 5" of cock was stuffed into my ass, and while the dildo had been longer, his cock was definitely thicker. He started to rock back and forth, fucking me with short, quick thrusts of his cock. The intensity of his fucking was causing me to rock back and forth, so he grabbed my hips to hold me still.
My head lay on the pillow as he fucked me, alternatively gasping at the pain and moaning at the pleasure. This is what I had dreamt of for so long, the feeling of being someone's fuck, being penetrated and taken. I was hooked. My cock was quivering, for every thrust he hit my prostate and nearly caused me to explode. I pushed back against him, fucking his cock, trying to get it deeper into me with every thrust. We just went onlike that, back and forth and back and forth, until he was ready to cum again. Now, when we were chatting, he andI both assured one another that we were disease free. But it was something taken on faith, and I didn't know if he had a condom on or not. I started to panic, my ass quivering as I wanted to pull away, scared if he was lying to me. Alan kept me tightly to him, fucking me, and with a loud moan he rammed his cock as deep as he could and then started spewing cum into my asshole. As I felt his first wave of cum splash inside me, I couldn't hold back any longer, and I started to orgasm, my own cock squirting cum onto his sheets under me. Alan held my hips as his cock emptied itself into me, completely taking my virginity now, and I writhed under him, loving the feeling. Slowly he pulled his softening cock from my behind, and the cum started to leak down slowly, as he grabbed a towel to clean me up.
His hands slowly wiped the cum from my ass, and he felt the wet puddle under me and smiled. "You enjoyed yourself I think." I lay next to the mess, smiling up at him, spent in more ways than one. He looked down at me from the side of the bed. "You need to go now, I have to get some sleep. But I'll be in touch, don't you worry." He helped me dress and showed me to the door, and I drove home in a daze, getting home only to grab my own toy, slide it into my ass, wishing it was a hard cock. Then it was just a matter of time until he IM'd me again...