Swing, Swing #1: In The Beginning, There Was Dick
A little bit of background information is necessary before I get into the nitty-gritty of my online escapades. First thing you should know is that I’m not straight but not bisexual either. I’m somewhere in between, in that limbo that can’t be described. The one thing I do know for certain is that I’ll always love women. I can be intimate with them and relax in their presence in a way that I never could with men. I can be romantic with them, and cuddle, and be vulnerable. Men, on the other hand, I’m hard-pressed to hug but I’ll take a cum-shot in the mouth and swallow with glee. I can’t tell you when I started to feel these desires but I can tell you about when I decided to act on them.
I was fifteen at the time, dating the hottest girl in school and getting amazing sex on the regular. Bless that girl. We were ‘in love’, a concept that I believed in back before I realised that no woman is truly yours; it’s just your turn. Sexually, she gave herself to me in ways that I’m forever grateful for. To date, she’s still one of my top three lays but there’s something I wanted at the time that she just couldn’t give me- a cock in the ass.
We were in boarding school back them, so you could say that there were plenty of opportunities to sneak into the showers with one of my dorm-mates but that wasn’t an option for me. The only way that I could indulge in this pleasure completely was if I knew that there no way it could come back to me. I wouldn’t be able to live with the knowledge that whoever I hooked up with might let it slip to someone who let it slip to someone else who let it slip to the whole world. If that happened then I’d end up with a reputation for being that guy who gets bummed in the showers. I couldn’t risk being attached to the stigma, so I had to get my rocks off somewhere else.
The internet stood out as my best option because of the anonymity that it offered. I could just put up an ad or a profile detailing what I wanted without surrendering any of my personal information and let the like-minded freaks find me. I didn’t want to pay anything for full membership on the site so I snuck my phone number into my profile handle. That was a big mistake.
Over the next few months, my phone blew up. I got messages and calls from guys all over the country who wanted a taste of my ass. That was the moment when I realised why women are always on their phones- they’ve got guys trying to get into their panties 24/7. I had no interest in banging all of them so I picked one at random and we set up a date at a seedy hotel in town. The fact that I was underage didn’t seem to bother him at all. It just meant that we had to be extra sneaky.
The day had finally come. After years of dirty fantasies it was finally time to get my first bumming. Sure, I’d stuck a few fingers and even pens up there but I could never get deep enough or hit the right spot. And the pens were uncomfortably sharp. What I needed was real dick, and now I’d have it.
Was I nervous? Hell yeah. I didn’t even know what this guy looked like. All I knew about him was that he wanted to use my body to fulfil his own desires. What if his desires went beyond penetration? I’d be found strangled to death in a hotel room in the middle of nowhere with an asshole full of jizz.
The fear almost made me bail. Eventually I mustered up the courage to get up and go. This was what I wanted. This was what I dreamed about while jerking off with a finger in my ass. Now I’d learn what it felt like to be stretched out.
I can’t remember for certain but I think I wore white that day. A symbol of the anal virginity that I was about to give up. Whatever my reason for wearing white, that was how I told the guy to recognize me as I stood outside the National Archives where we’d agreed to meet.
He found me easily enough and guided us towards a hotel in the seedier parts of town. Our story for the receptionist at the hotel was that we were a pair of brothers travelling from Western and we needed a room to crash in while we waited for the next bus to coast to depart. The receptionist gave us a look like he knew what we were up to but we probably weren’t the first pair of ‘brothers’ who needed a room in that place. The only possible issue would be my age. Maybe the receptionist was trying to size up if I was there of my own volition. I kept my eyes down and avoided eye contact. The desk-guy eventually shrugged, grabbed a key and led us up to our room. It was a terrible room. The kind that you didn’t want to risk getting under the covers in because you couldn’t be certain about the last time they were washed. But it was good enough for the purpose that we had in mind.
Once the door was I closed I started to strip. If I took a second longer to think about what we were about to do, then I would have bolted. The dude, for the life of me I can’t remember his name, took the hint and started to strip too.
Then we were both naked, standing there awkwardly as if we didn’t know what to do next. I got the feeling that he would move in and start trying to kiss me or something romantic like that and that was the last thing that I wanted. Nothing turns me off faster than a man trying to seduce me like I’m a woman. So I took the lead, dropped to my knees, cupped his balls in my hands and put his shaft in my mouth. That was the first time I’d had another man’s meat in my mouth and my performance was far from inspiring. It just wasn’t what I expected. I mean, pussy has this sticky-sweet odour that draws you in but ball-swear is just dank and musky. Regardless, I carried on with the task at mouth, knowing damn well that I was giving him the worst blowjob of his life. I knew enough not to use teeth but that was about it.
The sequence of events is a bit blurry but eventually I ended up on the bed with my belly down and ass up. He pulled out a packed of ribbed rubbers and I nearly laughed. Did he really think that ribbed made a difference?
They didn’t.
He rubbered up and got on top of me. Started to explore my ass-crack with the top of his dick. It felt like I was being probed by a baseball bat. He struggled to find the hole and when he eventually did, I gasped in pain. It hurt. It hurt like hell and he hadn’t even put it in yet. It wasn’t going to fit that way so we switched up positions and tried doggy. Same problem. I got on top and tried to lower myself onto him but that hurt even more. By this point the dude was losing his motivation too. His wood lost its hydraulic pressure with every failed attempt until it was like trying to fuck myself with cooked spaghetti. I sighed and got off, resigned to the fact that I wouldn’t be getting bummed that afternoon. The other guy sensed it too, but he’d already paid for the room and his underage twink was there. One way or another, he was getting his rocks off.
He instructed me to lie down on my back then laid on top of me with his cock squeezed between my thighs. He proceed to flop away on top of me and the full-body contact made me want to gag but I shut up and let him do what he had to do while I stared at the ceiling, wondering what the hell I was doing there. Thankfully, he was quick on the draw and got off me when he was done, leaving a puddle of warm cream dripping down my thighs and onto the sheets. He looked satisfied enough so I cleaned myself off and got dressed. We decided that it would be best if I went down first, just to allay any suspicions. I agreed, stepped out and didn’t look back. Went back to my normal life like nothing had happened, but determined to try again.