Puppy Love Turned To So Much More

[If you want to skip the backstory and get to the details about the event itself, skip to paragraph 5]

It all started when I was 14, I had a crush on someone at my school. Although being immature with his friends, he was seemingly shy but sensitive enough towards me. He at times responded to my minority flirtatious gestures which led me to question his sexual orientation, but when another friend of mine (who also had a crush on him) asked if he was gay, he bluntly said no. Fast forward 3 years, somehow he found out about my feelings towards him, which led to a year of ongoing friend-zoning as a kind of joke between us, but little did I know that in our last 2 weeks of school things would change beyond what I ever could have imagined.

On the 2nd of September, he had recently turned 18 and went out drinking for someone else’s birthday. I was 17 and stuck at home doing homework. He messaged me that Saturday night and was not just more talkative than before, but also took a while to type out simple texts. Out of concern, I stayed up and called to checked in on him every so often. Eventually it hit 1 am the following day and he was extremely drunk and wanted to take the train home. Having seen all the stories about drunks falling off the tracks or getting mugged, I suggested I’d come pick him up. So at 1 am I drove all the way to the city to pick him up. He’d never been drinking before and so was understandably worried about his parent’s reaction, so we ended up staying at an apartment I had in the city that night, and the plan was the next morning he’d sober up and go home.

When we got there, he had a shower and came out wrapped in a towel. We talked for a bit before he suggested we go to bed. Because all this was unplanned, he had no PJs so was going to sleep in his undies. As he got up I pulled away his towel (knowing that would be my only and last chance) and he just laughed and put his undies on. He got into bed, shaking non-stop due to the alcohol. I decided to stay with him to make sure he was ok, and we talked for another 2-3 hours about school and the daunting future beyond high school. It would’ve been 4 or 5 am and we were both so exhausted that we fell asleep in the same bed, nothing sexual, nothing intentional. I should mention, whilst he was almost naked, I was clothed.

I assumed most straight people in that situation would be on the furthest edge of the bed, turned away from me, but he didn’t. He often faced me, even shuffling himself such that his head was close to mine and our legs were gently touching. Some 10 hours after I’d picked him up, I rested my hand against his shoulder and my head against my hand. This is when it began.

He turned to face me side-on and reached over to hug me, I was confused but obliged nonetheless. We hugged for a while at which point I looked into his eyes and saw panic. I asked him what was wrong and he whispered “I don’t know, I’m just freaking out”. I moved in and gave him a peck on his warm cheek saying “it’s ok, trust me, it’ll be ok”. But then I realised, maybe it wasn’t ok with him, and I’d heard of the self-harm some people do when they do something they regret, so I told him “Look, if you sober up and realise what’s happened, please don’t do anything stupid. I just want you to be happy in the future” to which he replied “You know what Lobbo, I’m pretty happy now”. He smiled at me, with a look of genuine happiness and contentment and then we made out. I’d never done it before, but once he began bitting my lip and feeling around with his tongue, everything felt natural and his warm, soft lips felt unlike anything I’d ever experienced before.

We then turned, fully facing each other, just hugging, and I rested my head against his chest and he put his head against mine. I was half quite literally living a dream, but the other half was so confused and panicked. He then lifted one of his legs to allow me to interlock our legs, at least that’s what I thought he meant, because he just laughed when I did. I stroked his back as we hugged and slowly lowered my hand until it was over his bum. It was then that I felt him push his groin into me. I could feel his erection under his boxers and stroked it before he took his undies off all together, letting me stroke his dick.

It was slightly longer than mine, but otherwise much the same. I gave him a hand job, but what I never anticipated was how tiring it was! The angle of my arm was not convenient, and he took longer than what I had expected. He just lay there, eyes closed as I continued to stroke him in the dim light hid by the curtains, but several times I let him do it himself as my arm needed a break! Again, it was a first for me, and watching him, I realised he preferred it slowly stroked. I took back over and made the biggest leap of faith when I lowered my head, sucking his scrotum and the head of his penis; it was much wider than I had expected!

After some time, he grabbed the top of my head pushed it into his crotch, the first few time nothing much happened, probably because I couldn’t keep up the momentum of my hand given I was lying next to him and that my head limited the hand movement. But eventually he gently pushed my head down and I felt his slim body convulse, pushing his penis into my head, breathing deeply. I don’t know if he did have an orgasm that day because nothing came out (at least that I tasted or felt) but something happened for sure.

We lay there in silence, my head against his chest. I could hear his heart beating rapidly. I had message his mum the previous night telling her that he was with me and she said she would pick him up early afternoon. I looked over to the clock, and given the time was 11 am, I suggested we have a shower and go for something to eat before she arrived. So I took of my clothes and hopped in the shower and he joined me. We washed without speaking, ironic given that just a few days ago our messages (remember he was often flirtatious but friend zoned me as a joke) read something like:
Me”brb, gotta go do something”
Him “(winky face) I know what that means”
Me “Chill, I’m just gonna have a shower”
Him “If I said that, you wouldn’t be chill”

I passed got him a towel and we dried off, putting on our clothes from the past night, and headed off for something to eat. After an experience I can only describe as surreal and confusing, everything went back to normal… between us two at least. I still don’t and probably will never know why what happened did happen, if he ever did feel something towards me, or even if he is gay or straight. But I am content knowing that regardless of that one night, we have remained good friends. I’d like to say it was happily ever after, but everything blew up between a whole range of people for no real reason. But that’s another story.

~Lobbo



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