This is just the first chapter of a series I have in mind. It won't all be gay. In fact, most of it won't be, but this one DEFINITELY is.
All characters are at least 18 years old or older.
**********
I'd always been a go-with-the-flow type of guy. Being raised by parents who questioned almost all social norms, I was never forced into a mold like "man's man" or "male feminist." I was only told to respect everybody so long as they don't wish to cause any harm. My father even had a sign made up that he put above the walkway to the kitchen. It simply read "Don't Be An Asshole." That was the only position of mine I would defend to my very being. Everything else was subject to change.
This outlook on life made me very popular growing up because I never judged people. Yeah, there were jerks, but they don't bother you too much if you're friends with everyone else. I liked everybody. I was friends with white kids, black kids, straight kids, gay kids, jocks, nerds, and even a few high school faculty(shhh). The trick was I treated them all like best friends, not just my own, but each other's. I'd invite the nerds to the jocks parties and try to talk about things that I felt they both liked. Things like movies, comics, and always—always—women.
Because I treated everyone like my best friend, more than a few put me into their inner circle. It seems like every day someone was telling me a secret about themselves. For some, it was simply who they had a crush on and asking for advice, for others, it was really personal like having to deal with abusive parents and their sexuality. I listened to all and never treated them any differently.
I suppose I should mention I was never in a relationship while attending school. Don't get me wrong, being so accepting of people did lead to a few—quite a few, actually—crushes, both on my part and theirs. But, you see, everyone has a story to live, and I never felt I should be that part of someone's story. There was always a reason I could find that I couldn't be with someone. Maybe I thought they would be better suited for another, maybe I thought I could be of more use to them as a friend and not a boyfriend, hell, one time I didn't go out with a girl because I was pretty sure she was a lesbian and was just in denial (I was right btw). I guess I felt as if it was my duty to make sure my friends were happy before me. I know I'm such a good friend. Humble too.
That said, by the time I graduated high school, I was anything but a virgin.
**********
My first sexual experience came with my friend, Michael. Mike was a rich friend with absent parents. Of course, he was more than that, but that's what got told to those who had never met him. Looking at him, you'd think he was the stereotypical preppy dudebro and you'd be right. He was given a brand new Mercedes for his sixteenth birthday, he didn't have to get a job because his parents gave him a sizeable weekly allowance that should have qualified him to pay his share of taxes, and he called everyone "my dude." In all seriousness though, he was just lonely, and throwing parties were the only way to be acknowledged in his own home. I knew this because he told me as much when we were hanging out late one night. Nothing like getting high at 1:00 am to get someone to open up. After he confessed to me he seemed to talk to me more and invited me to hang out at his place more often. I think I was the only person he talked to between parties.
I was hanging out at his place just before school started in the fall when the conversation turned to porn. I wasn't sure what brought it on, but it was something I was very familiar with so I went with it.
"I'm more into dom/sub shit, you know. I mean nothing is better than seeing a girl desperately gagging while trying to please a cock." He said just before taking a hit of his blunt. "Nothing like it, my dude." He said just before he exhaled all the smoke in his lungs.
"I'm not surprised. A lot of people are into that. Hell, I can't tell you the number of times I've busted to a Perv City video." I told him. I wasn't smoking because I was more of an edible guy and I had a cookie just an hour before.
"Oh, I love their shit. They make the girl gag and drool on that cock for like 20 minutes then make 'em stand up and put it in their ass. God bless America." He chuckled as he faux saluted.
"Well that's almost all of them, but what would you say was your all-time favorite video? it doesn't even have to be Perv City," I asked him. Mike's face made it look like he'd been waiting for an excuse to bring it up. Without a word he pulled out his phone and started casting to his 75-inch OLED TV (rich friend, remember?) and a video started playing right away. He had that shit queued up. I didn't say anything knowing he would shy away from me if I even teased him.
The video jumped right into the action with a cute short-haired blonde crawling between a dude's legs. The camera was off to the side; close to the girl's head. She unbuttoned the guy's pants and dragged them off. Guys in these things never wear underwear and this one was no different. His cock flopped out and stood tall. She looked at it hungrily and licked her lips. She barely kissed the head while gently grasping his shaft. She looked up to the man's face with a beautiful pair of puppy dog eyes.
"You want it?" The man in the video asked her. She just nodded at him with her pleading eyes. "Then get ready, slut." The man reaches out and grabs the back of her head and forced his cock into her eager mouth. For the next 15 minutes, we watched in silence while the cute blonde worshipped the thick cock. Spit going everywhere, the guy forcing his cock down her pipe and holding it there until she looked like she was going to pass out, then when he let her up she was eager to do it again. I gave her a lot of credit, if she was acting, she was doing a great job.
Occasionally I would look over at Mike and I would see him fidgeting with the crotch of his pants with one hand while combing back his own blonde hair with the other. And he was biting his bottom lip...HARD. I think he was really getting off right next to me. I was hard too, but I wasn't just going to start touching myself next to my friend. I noticed that he would tense up when the man would degrade the cocksucking blonde. Calling her "slut," "whore," and my personal favorite "fucking bitch." I felt that maybe I should let him be alone so he could take care of himself. I was about to get up when I heard something strange.
"Take that cock, you fucking faggot."
Mike immediately reached for his phone to try to stop the video.
"You are a faggot, aren't you?" the man asked. The woman took the cock out from where it was buried deep in her throat.
"I'm a cocksucking fagg—," she was cut off by Mike finally ending the cast. We sat in stunned silence for a few seconds. I was just reeling from the revelation that he got off to a transsexual woman, albeit a very cute one. I thought he was as straight as they come. In fact, part of me assumed he may have been transphobic. That's the last time I assume about people. Then I realized he probably didn't mean for me to hear that. I look at him and he is staring at me, eyes wide, gauging my reaction. I wanted him to know it was okay and I didn't think any less of him. I needed to word my response very carefully.
"It's okay, my dude," was all I could come up with at first. "I thought it was hot too. She really knew how to work her mouth," I said while looking away. I couldn't help but feel I wasn't supposed to know this about him. He looked at me without saying a word for at least 30 seconds. I reached out to him and placed my hand on his shoulder. "It's okay, really. No big deal." I tried to reassure him. His lip started to tremble and he proceeded to break down and started weeping. I brought his head to my chest and let him cry it out. I didn't think it was that big a deal. As I said, she was pretty hot. Definitely passed. It wasn't long before he stopped crying and I saw that he fell asleep on me. I thought about leaving, but I didn't want him to think I abandoned him so I just laid back on the pillow while keeping his head on my chest. I just lightly played with his hair until I fell asleep too.
I woke up sometime later laying on my left side, spooning Mike. Like proper hand-around-his-waist-and-body-contact-from-chest-to-legs type of spooning. I looked over to see his face and he was still fast asleep. I admit I was a little slow to see that the light had been turned off. Did he turn it off? His parents were still out of town for another week and he was an only child so it had to have been him. That means he intentionally got back into bed with me and possibly moved me to cuddle with him. The last part was only supported by the fact his hand was covering mine as it sat on his flat tummy. It was then I looked him over, lit only by the full moon shining through his sliding glass door leading out to his terrace (rich friend, remember?).
His build overall was lean and slim. When standing up I'm about a head taller than him so I'd put him at about 5 feet and 8 inches tall, give or take. His curly hair was blonde and shaved very short along the side. Some have joked it was the stereotypical fuckboi noodle cut. It was in good fun and I know he just wanted to fit in. It suited him if I were honest. His face was always clean-shaven. I don't think he could grow facial hair even if he wanted to. As I scanned downwards I noticed he had taken off his shirt at some point because I could see and feel his bare skin underneath my hand. I looked further down and sure enough, only his boxers were still on.
This was when I really started to rethink some things. I had assumed that he fantasized about making a trans woman into a slut, but looking at how he broke down afterward, and his assuming of the small spoon role while mostly naked, I started to think maybe -just maybe—he wanted to be the one to be degraded and used and he was ashamed of it. As I was thinking it over, Mike had stirred in his sleep and brought my hand up to his chest while scooting his ass back into my dick.
I should mention that I never gave my sexuality a label. I liked who I liked. Whenever someone tried to pin me down to an answer on the whole straight or gay thing. I would tell them my spank bank is rated E for everyone (within reason, obviously). I wouldn't even comment if asked if I was a top or bottom. As if my virgin ass would know.
I tell you this to let you know that I was not surprised nor conflicted when my cock started to get hard. Ass is ass and this one was grinding on me. Soon my cock was rock hard in my jeans and pressing into Mike's ass. I didn't know what to do because Mike was still asleep. At least, I thought he was until I noticed his breathing had become irregular.
He was awake. He was awake and flexing his ass. I pushed forward into him, making sure he knew I was awake and enjoying it. He let out a soft moan. I moved my had over his nipple and he gave a quick inhale as I slowly started rubbing it. I leaned close to his ear.
