I had my group of friends. We had been friends since early on in high school, and though we had since become a lot looser of a friend group we still tried to spend as much time as possible with each other and could talk to each other about things that we couldn’t to anyone else, or just ‘be’ without worrying. We were each other’s oasis in the wilderness of high school – it was quite amazing that we could find each other to not be self conscious around. I was bullied. They were not bullied as much but also didn’t fit into any specific crowd, though I suppose we were some kind of a subgroup of the nerdy, geeky people who we hung around a little bit, but who we couldn’t identify with as much as they could with each other. We were into a lot of the same things but maybe it was that we were into it differently or something? I don’t know what it was exactly, but somehow we found each other. Even if we didn’t have interests or identities that matched perfectly we were open to learning about what each other was interested in. It ended up meaning that we weren’t just friends because we had identical musical tastes or anything like that, but because we could relate to each other in a more… basic kind of way. After high school we ended up all in pretty different places in our lives but we still got together sometimes.
Cassie, Andre, Luke, Fiona, Simon, Lela and me.
Cassie was into sewing and so was Lela a little bit. I learned to sew from Cassie and so did Andre, a bit – enough that I can follow a basic pattern anyway. Luke and Fiona tended to know a lot about all different kinds of music – they introduced me to a lot of music that I listen to now. I tended to be the closest to Simon, and would hang out with Simon most.
All of them were cis gendered and tending towards being straight and so when I tried to explain how I was feeling around gender they thought that I was trans, which was really only partially true. Or they thought that maybe I was gay. These were just categories that they already knew of that they resorted to, but they were open to it being different than that and to referring to me as ‘they’ rather than ‘he’.
Sometimes there would be periods where two people in our group went out together for a little bit or something like that – Cassie and Andre were together for the longest time so their dynamic was the most absorbed into the group but other than that it just created awkwardness and it seemed to generally get dissolved because it turned out that it was better when we were all just friends. I seemed to be the only one that didn’t go through the “dating my friends” period in the group. People seemed to think that Simon and I should be together – again the assumption that I was gay or at least not attracted to women played out in this way, as they never seemed to think of the possibility of me and any of the girls being together.
“The others think that we’re into each other,” Simon announced one day quite abruptly.
“Yeah. They do. I think they still really think of me as gay even though I’ve explained that I’m not.”
“Yeah… I think they do. I try not to see it that way but… I mean I get it kind of, ‘cause I’m mostly interested in females but I don’t rule out the possibility of others.”
I wasn’t sure what to think of what he was trying to say. Was he saying that he liked me? It definitely seemed like it. But what kind of invitation was ‘everyone thinks that we should be together’? The second one about not ruling out ‘others’ sounded more like an actual invitation but… what was that? Really a really negative kind of one anyways. What kind of an invitation was “most of the time this is never a thing but there’s a slight bit of a chance that it might be…” This was no decent invitation either. Honestly maybe I was just oblivious but I never noticed Simon seeming to have any kind of feelings towards me that were romantic or sexual and neither did I towards him…
“Simon, are you actually interested in me or are you just saying stuff because you are wondering if you are into people who are non female too?”
I replied with the same amount of bluntness. I suppose it said a lot about our friendship that we were so blunt with each other about sensitive subject matter without fear that we would hurt each other. Well, I suppose the bluntness with which we said these things also made them less sensitive. “Maybe.”
“Well, we should kiss then,” I said.
And with surprisingly little awkwardness we kissed at first just once on the lips before we separated and looked at each other.
“Okay,” Simon said.
“Yeah that was okay.”
“But it wasn’t much but a taste was it?” said Simon and put his arm around my neck and drew me in. He opened his mouth and I opened mine and he put his tongue in my mouth. I put mine in his. This lasted for a surprising amount of time. We enjoyed it.
“That was good wasn’t it?” asked Simon.
“Yeah, it was. I still don’t feel romantic about it though.”
“Yeah. Me neither. That was your first time wasn’t it? Sorry… I feel like I stole it or something. Your first time and it wasn’t even romantic. I feel bad now.”
“Don’t. I don’t care. I didn’t have any ideals about my first kiss or anything. You know I’m not a romantic.”
“Okay. Yeah. I won’t feel bad then as long as it was good.”
“Yeah it was,” I repeated.
We made out a few times and eventually this led to sex. There was only a little bit of hesitation as to whether this was going too far but not that much. It seemed a natural progression of our many making-out sessions. We mutually masturbated which within a few times lead to oral sex.
“I feel like all we do is make out and have sex now. What happened to just hanging out?” I asked.
“Yeah… you know we should really spend time together outside or somewhere else public rather than at each other’s places so we won’t just end up making out or having sex or cuddling.”
“Not that this is a bad thing.”
“No.”
So we did start to meet up outside or in other public places. Although we did end up kissing or being a little affectionate in these places too.
The next time we got together at Simon’s place he asked: “So, do you want to have ‘sex, sex’?”
“But we have been having ‘sex, sex’.”
“Okay. Well, you know what I mean.”
“You mean anal sex.”
“Yeah, I mean that.”
“Because I don’t know what your definition of sex is but mine is anything that leads to or is an attempt of arousal and maybe orgasm?”
“Yeah… I never really thought about it in that much detail but I agree.”
“So, anal sex?”
“Yeah. Actually since I thought you might be into it I bought some lube...”
“Well, you know, for our first time doing this together and for it being my first time I’m not comfortable with being the one to receive… ‘cause well, I feel like normally it would be that way because you are the more masculine one, but I’m not comfortable with it because of that. I feel like it would be reaffirming gender norms and saying that for me to be less male and more female, in the middle somewhere I have to be the submissive one.”
I could tell that Simon was a little puzzled, probably because he was expecting me to want to be the one to bottom and because he had never thought about it this way before.
“Okay. Yeah. I can get that.”
“So are you comfortable with this?”
“Yeah.”
“Are you… nervous at all?”
“Yeah, a little. I mean I don’t know but I imagine that it will hurt.”
I slid my hand down his pants and rubbed his bottom and squeezed it. This made me really hard.
“I’ll go slowly,” I said beginning to remove his pants. “Are you sure you’re okay with this?” I asked, removing my hands from him and removing myself a little bit from him. I didn’t want to end up coercing him into anything by my beginning it and not stopping and therefore leaving the only option for him to be a “yes”. I stuck my hands between my legs and closed them tight around them to show that I was able and willing to stop if he didn’t want to do this.
“No, I really want this too. Being a little scared doesn’t mean that I don’t want it. I do really want it. I just want you to go slowly and gently.”
“Yes, I will.”
He put his hand on me and started to undo my pants. I undid his too and soon we were naked. We kissed and I pushed him down onto his bed. Putting a condom on and lubing up, I started to insert slowly – he was very tight.
“Are you okay?” I asked, rubbing his shoulder.
“Yeah, I am.”
I thrust in a little more and he made a little bit of a hurt sound.
“Still alright?
“Yes. It just hurts.”
“Should I stop then?”
“No, it’s good hurt.”
I thrust in farther and he made more hurt sounds. I reached under him and grabbed his dick. It was very hard. I rubbed it as I drew myself in and out until I came.
“Will you stay in me while you jerk me off?” Simon asked.
So we repositioned so that he was sitting on me, with my penis still in him though it was a little difficult to because I had become soft, while I jerked him off until he came.