This story is excerpts, extracted and gathered together from the NaNoWriMo story I attempted to write when I was 19. I did reach the required word count within the month, but I never did anything with it afterwards so the whole thing had been left an unedited word vomit for 8 years. Though not very “sexy” it felt pretty affirming to my self to write this when I had done so and therefore I figured that I would share this here… although it is pretty much unedited! I am sorry for the mess that it is, and for the fact that it might be pretty boring…

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.”


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?”


“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.

I pulled myself fully out of him and we cuddled, naked with Simon sitting on my lap.




My mother was surprised by my decision to move out but tried to conceal it as best she could so that she wouldn’t make me feel bad.

“Well, that’ll be good won’t it?” she said.

“Yeah. I mean I’m not moving away because I don’t want to be with you. I just think that, yeah, it’ll be good. Something different you know? And I want to try living on my own,” I said, feeling rather defensive of my legitimate life choice.

“Yeah. Yeah, it’ll be good,” my mother repeated.

My mother didn’t have a car nor did she drive. I didn’t have a car either but at least I had gotten my license so I could drive – I borrowed a van for my moving day. My collection of music, movies and books took up the most amount of space in the van as well as effort to haul.

Simon came over to help. My mother was also under the impression that we were ‘together’, as were all of our friends.

“Hi, Simon. How are you doing?”

“Hi, Caitlin. Oh, pretty good, pretty good. Working, going to school a bit, you know, kinda just the same as usual. You sad about Sam moving out?”

“Well, of course I am! But Sam should do what they want to.”

My mother and Simon got along. If they didn’t our friendship probably wouldn’t have worked out too well.

“Andre and Fiona are going to come over to help too,” said Simon.

“Oh, okay! I didn’t realize they were coming. I thought that everyone else was busy.”

“Yeah, well I guess they aren’t. It’s a pretty big event, you moving out. You’re only the second one of us to move out.”

“Yeah, well, that’s great!”

So, with many hands work was made light and the boxes of books, music and movies and a few other things that I had packed were moved into the van and into my new basement apartment pretty quickly during the morning. Our mission in the afternoon was to hit up some thrift stores and get a few pieces of furniture and hopefully a few things for the kitchen. So we headed over to the area of town where there are a lot of thrift stores. My mother didn’t have many things she could spare, but when people heard that I was moving, friends’ parents gave me a few things.

“How much money have you got for this?”

“Uh… not much,” I said fishing out my wallet.

“Well, what do you need the most then?”

“Let’s see… took the bed and mattress and a couple of bookcases from mom’s… uh. Pots, kitchen stuff like dishes would be good. Maybe a kitchen table? A couch? That’d be good.”

We jumped into one store after another, leaping onto the couches to check for comfort, banging the pots to check for the sound. They teased me by saying that I needed to get all sorts of completely ridiculous or gaudy things. But we did find things that would be useful and were nice enough and I only ended up with about three dollars worth of strange kitchen things that I wasn’t sure if I’d use.

“This is the biggest couch so far, Sam. You gotta get this one. If there’s one thing that you need to be big it’s the couch. The bigger the better!”

So we ended up with a fairly sizable couch.

When we got to my place and unloaded everything there was a pile of boxes and some furniture in the middle of the main area. I drove the van back to the rental place and we got pizzas and beer and went back to my place again. (At that point I liked any excuse to say ‘my place’.) We got pretty full on the cheesy doughy pizza and a little drunk too.

“I gotta work tomorrow so I’d better head out,” stated Fiona.

“Yeah, I’ve got class in the morning which I should be alive for,” said Andre.

“But there’s still beer, guys, that ain’t right,” said Simon.

“Yeah… another day. I should really get going.” – Fiona.

“Yeah. And we can leave you guys to it here all on your own at Sam’s very own place, eh?” Andre winked very deliberately as they gathered themselves up and left.

“So, I guess we’ve been ‘left to it’ eh?” laughed Simon.

“Yes we have, haven’t we?”

“Well, with this whole place to ourselves, your very own place, we could fuck just about anywhere we like couldn’t we?”

Simon grabbed me by the back of my pants and pulled me to himself and started to hump me, sliding his hand down my pants and grabbing my butt.

“Yes we can fuck anywhere we like. Anywhere at all,” I said, guiding his hand onto my hard-on and into my pants, undoing my belt.

I was so aroused that I almost immediately became vocal in my pleasure.

“Anywhere, eh?” said Simon and grabbed me this time by the back of my collar and pushed me onto the kitchen table.

“What would you say if I said that I really feel like spanking you right now?” asked Simon.

“I would say: do it!”

He pulled my pants down and started to spank me with his hand with a surprising amount of force, sometimes rubbing or squeezing me in-between.

“How are you doing now, huh?” asked Simon, pulling my face up by my hair. I was experiencing so much sensation and emotion all at once that I was barely able to say anything at all – all I managed was a groan. Simon let my head go and reached under me and grabbed me.

“Well, you’re hard as fuck. You must be enjoying it huh?”

All I managed was a groan, again.

“Well, I can’t continue unless you give me some words for how you’re feeling about this, ‘kay?” he said, flipping me over onto my back.

“I am enjoying it,” I finally managed.

He kissed me roughly and quickly, tugging my hair away from my face. He quickly inserted me into his mouth for a few seconds before flipping me over again and, with force, started to spank me again. He started to hit me with his belt which he used with increasing force.

“How’s this huh?”

“Good. Painful. Good.”

“How about you call me ‘sir’. I’d like that. Would you like that?”

“Yes, sir.”

“When you talk to me you’re going to reply with ‘sir’ at the end then. Huh?” he said, pulling my face up by my hair again.

“Yes, sir.”

He continued on for quite a while and it was starting to get pretty painful.

“Fuck that hurts.”

“What was that, huh?” Simon panted, obviously exerting a lot of energy for this.

“I said… fuck that hurts.”

“Huh?” He said and flipped me over again by my hair.

“Did I hear you say something without ‘sir’ at the end?” he asked and slapped me across my face.

I was a little surprised and taken aback. But right after he kissed me, forcefully pushing his tongue into my mouth, I kissed back.

He whispered to me: “Sorry I slapped you. I think I’m a little carried away.”

“No. Don’t be sorry. It’s okay.”

“How are you doing?”

“Good, sir.”

“Can you take more?”

“Yes. Yes, sir, I can.”

He flipped me over again and started to spank me once again with his hand and with his belt.

“Fuck, you’re red. I just wanna fuck you so hard right now. You okay with that?”

“Yes, sir.”

After just enough time to put a condom on he inserted himself. There was nothing slow or gentle about it this time, it was so sudden and quick that I yelled out.


“Yes…yes I am… sir.”

We were both hardly able to speak. He clapped his hand over my mouth to muffle my subsequent screams. But it really only took a few thrusts for him to come. He pulled me up, still inside of me; he was panting and hot and sweaty. He hugged me close to himself and started to jerk me off. I also came very quickly – he aimed so that I came all over the kitchen table. He grabbed me by my hair again pulling out of me and forced my face towards the table.

“Now, eat it up. Huh?”

“Yes, sir.”

He knew that I enjoyed the taste of my own cum. When I was done he pulled me up by my hair once again and licked off the cum that I had gotten on my face and stuck his tongue inside of my mouth. We kissed, finally relaxing out of our extremely heightened sexual state.

Simon took off his condom and threw it out and we collapsed onto the couch in our half undressed state – I had never actually fully removed my pants and still had my shirt on and Simon had taken his shirt off but had pulled up his pants though they were not actually done up.

We started to laugh with abandon as we cuddled. Simon slid his hand up my shirt and rubbed me – I was also very sweaty.

“Fuck, that was hot… I hope you enjoyed it as much as I did,” said Simon.

“Yeah, fucking hot,” I agreed. “Sir,” I added which made us start laughing all over again.

“You don’t have work tomorrow, do you, Sam?”


“Well, that’s good ‘cause it’s… let’s see… about… uh, one AM now.”

“And you don’t have anything tomorrow?”

“No, I haven’t got anything on any Sundays.”

“Well, you should sleep over then.”

For the first time we slept through the night together, naked and spooning, cuddling together all night on bedding spread out on the floor of the bedroom because the bed wasn’t set up yet.

In the morning we found some of the groceries that I had bought before the move, as well as some of the cooking utensils and made pancakes. After which I located some music and something to play it on, and we started to unpack some things, putting them in order. In particular the kitchen stuff and the bigger things like the bed that I would not be able to move by myself as easily.



This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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