This is the true story of the time I lost my virginity to Mike, an older man I met on the internet. I will always remember my times with Mike. His cock was one of those rare, perfect cocks that you can always recall in your mind in a second, so every time we fucked was memorable. I hope you enjoy our first time as much as I did.
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For as long as I can remember, I craved cock. And I mean I really craved it. By the time I was a senior in high school, my sexual fantasies revolved around big, juicy dicks with cum cascading down them for me to lap up. I practiced blowing anything vaguely cock-shaped and I'd swallow my own cum. I dreamt of a cock swelling and emptying cum into my virgin asshole. Instinctually, I knew I was a total bottom. In the core of my sexual identity, I always knew my truth. I was the submissive receiver. I think any total bottom will back that up, pun intended.
What was strange about all of this was the fact that I wasn't attracted to any guys my age. I wasn't really attracted to any gay guy, I just found the prospect of getting fucked and sucking a cock intensely arousing. I felt so slutty with no avenue to be slutty. With no idea how to solve that problem, I was a virgin who watched vanilla gay porn and jerked off.
Once I got to college, I found other ways to explore my gay side. As a slender white boy and total bottom, I had no desire to use my cock as anything more than a clit with guys. Living in a single dorm had its perks. I began smoking weed in college; being high makes me so submissive and horny for cock it's absurd. I became insatiable when stoned. After jerking off to the idea of fucking myself, I caved and bought myself a real 7 inch dildo; I had it in my ass 24/7. I would get high and use gay chat roulette, riding my dildo for anyone with a nice cock to watch. I never showed my face though.
One day, I stumbled across a video that started me on my life-altering course towards Daddy cock. Videos seem to have that power over me. It was a video of this slender boi moaning as an older man fucked him bareback in missionary. The older man grunted as he fucked the boi roughly until he shoved his dick balls deep. The boi responded by moaning, "Daddy," as the older man seeded his hole.
My entire identity came into sharp focus as I watched the cum dribble out. I liked older men! That was it! I was a fucking slut for older men! I wanted to date them, I wanted to cuddle with them, I wanted to call them Daddy. I wanted to be their boy to dote on them, run my hands through their hair or their beard, feel their rough skin against my smooth skin. It was so simple, how did I never realize it?
Pretty quickly every older man became the sexiest creature alive to me. I loved everything about them, their graying hair, their slight wrinkles, and their veiny, rock hard cocks. I wanted to learn how to get them. Tumblr used to have fantastic daddy/son and sissy porn. It was ridiculous, I found every picture and video of older men fucking sissies who looked just like me. One picture drove me wild. A small twink making out with this older and muscular daddy while the daddy's thick cock is buried to the hilt in his ass. The twink was sitting on his daddy's hairy, thick legs in what seemed to be the perfect union. I was struck because I immediately thought of my anthropology professor, Steve. He always wore a well fitting dress shirt and tight dress pants during office hours, and his leg muscles stretched the fabric. This guy's legs looked just like Steve's.
Steve was a large man too, in his mid 50's, but built. He taught me anthropology 101. I smiled involuntarily while I thought of him, which was weird because I was always a basket-case of nerves around him. He was an attractive man, but comfortably attractive, like your friend's hot dad. His face was warm and inviting, and he had a cute twinkle in eye when he got excited about anthropology things. I thought about Steve's fit body. I always saw him running around campus and he'd come talk to me on the quad covered in sweat. I looked at the picture and thought, "I wonder if Steve fucks like that?"
Holy shit, why was I thinking about how he fucks? This could only end poorly. Admittedly, during our meetings, I would look for his cock's outline, because duh, horny 18 year old college freshman. But it was in a mindlessly horny way. But sitting there, stroking my little cock, looking at this daddy making love to a boy just like me. I was rethinking him. True, I was always impressed by him; he was in great shape and was pretty cute... Suddenly, the picture transformed into me and Steve, with me making love to Steve, milking his weighty cock with my ass, begging for his seed. I shook as a massive orgasm rolled through me and my cock exploded, sending cum all over my body. For the rest of the year, classes became hard for me, if you catch my drift. I unfortunately never got the chance to see Steve's cock, but he was the first real person I ever masturbated to while imagining him fucking me.
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I turned 20 and decided enough was enough, I was an adult and I wanted to get my ass fucked by an older man before I was too old to be a boi. I needed to lose my virginity fast because I knew part of my whole fantasy was being a young, small-framed boi. I wanted to be able to beg for a Daddy to pick me up and fuck me, and I wanted to beg him cum deep inside me while holding me.
In my desperation for cock, I signed up for a gay hookup site. I created a profile, listed my interests, and had a few nearby guys in the works. But nothing that really excited me. Then I got a message from Him. His username was BigCockMike and he lived close to me. I chuckled at the cocky name, but still clicked on his message. I was horny and jerking off, sue me. Besides, as you'll see, it worked out.
His profile opened and I saw his pictures. More importantly, I saw it.
I saw his manhood. His username was accurate. His cock had to be at least 8 inches and thick! My little penis stiffened. Just at the mere sight of it, my mouth started to water; I salivated over his large piece.
I was salivating over a cock yes, but I wasn't cock-crazy. It was totally justified for Mike's dick. For anybody as obsessed with men's dicks as me, a perfect cock is something to worship. Mike had a perfect one. He was shaved to boot, which let me behold the cock in all its glory. It was large, thick, and perfectly proportioned. The kind of cock that looks fun to ride. The kind of cock that you'd settle down with. The kind of cock that whispers to you sweet nothings. The kind of cock that was in a band, but in a cool way. It was hypnotic.
Mike's pictures gave many angles. I saw a vein run down the middle of the behemoth, and knew it was supplying the vital blood needed to allow the cock to swell to such size. I observed the head and how it was well-shaped and proportionate to the shaft. Like a work of art. It was a cultured, sophisticated man's cock. My little dick was as hurting just imagining getting to suck it and ride it. I found the first challenge for my ass.
I clicked on his other pictures. Mike was a tall, slightly-overweight and balding man. He was average looking and must have been very handsome as a youth. He also looked a hell of a lot like my father. Which, if I'm honest, really turned me on. He was perfect. I drank a bit of whisky and smoked a joint, so I decided to reply to him. He asked what I was looking for on the site. It was a hookup site, so I was blunt.
"Hi, I'm Matt. I'm really just looking for a big cock, preferably from a Daddy," I texted.
"Ha ha, then I think I might be of service," he replied.
"Yeah, it looks like you could be ;)" (Did I just send a winky face to a guy my Dad's age?)
"So are you actually 21?"
