Feedback request: Senior Year Pt. 03

I'm looking to improve my writing and hoping someone can give me some helpful advice. Anything regarding structure, character, dialog, grammar, or just general feedback would be appreciated. I'm also looking for an editor for part 4 if anyone's interested. Actually I had tried to find an editor for this part, but gave up after no one answered (which actually might be due to my email client).
The genre is gay male/first time.

https://www.literotica.com/s/senior-year-pt-03

I didn’t know Holden Caulfied was gay. That explains a lot. *smile*

I think your story is quite good and, mostly, so are your technicals (grammar, spelling, word usage, etc.). I was afraid you were starting off with too much background and physical description—I would have led with the encounter in bed, filtering in the physical descriptions during that, and then backtracked to some of the “how did they get there” background—but you kept it short and I’m sure there are readers who like it this way. Also, the chapters are quite short and could easily have been run together in longer takes, but they all include an encounter progressing to a full taking and there will be readers who like it this way. Be prepared, however, for the inevitable reader or two who will remark that any one-pager is too short.

There’s a slower pace and innocence to this that’s compelling. The setups are mostly quite believable (although I did wonder why stroking the belly when you have drunk nausea would be helpful other than to make you vomit) and I thought the dialogue was good and natural. I think the move to the bedroom could have been written better in chapter two, considering that you do have your protagonist think about what’s happening and sliding into naturally. A little more thinking by him that they were going to the same bedroom and what this meant and accepting it would have been better, I think. Thus, for me, this passage would have come better before they went into the bedroom than when they were already in bed: “In less than a week I was going to leave for college and who knew when I'd see him again. Did I really want to leave this question unanswered? I replayed in my mind the memory of him jerked me off, getting turned on and trying to work up the courage to do something.”

Also, in the natural state of things Chris is the aggressor here at least until they had broken the ice in getting to the next act toward going the whole way. So, it would have been more believable to me in chapter 2 if Chris orchestrated the sex on the bed more. He’s the one who set up the protagonist sleeping there. After they’ve had “all the way” sex, I could see the protagonist initiating encounters, but up to that point I see Chris as the initiator/orchestrator. There are just a few passages there where I don’t see Chris moving along on a seduction plan and I would have expected to see that. This is just my opinion, though. You wove it naturally enough that there will be those who like it the way it is and there’s Chris’ possible reticence in carrying through working here too, perhaps.

This I liked very much: “I was getting worked up fast and automatically slid down my boxers. He raised his leg and pulled them off completely with his foot.” Been there, done that, and I haven’t seen it depicted in a story before. I laughed (in a good way).

This sentence put me off a bit: “This was amazing, no girl had ever given me head like this before.” The setup you’ve given on his prior relationship with girls gave the impression that nothing had gotten as far as the girl giving him a blow job. And that it didn’t is natural to the story and the protagonist’s state of mind on sexual preference. So I would have dropped the “like this” as not needed anyway.

You are making everything so believable and even paced up to the middle of chapter 3 that I don’t think you spend enough time on the actual anal fuck in chapter 3—both the emotional side of it and the pain that is inevitably involved in it, especially the first time. To be natural/believable there needs to be shock mixed into the pleasure and meeting and overcoming the pain to get to the pleasure.

You have trouble with numbers. It’s “nineteen,” not “19,” for age; “six foot,” “not 6’,” for height; “six inches,” not “6 inches” and “two miles,” not “2 miles” for length; and “fifteen minutes,” not “15 minutes” for time. The “140” pounds is right, though. (The rules are complex but generally anything below 100 is written out—generally; there are exceptions.)

“Peak” for taking a glance was a gaff (should be “peek.” A “peak” is a mountain top) and “Ok” is not either “OK” or “okay” and should be one of those two, consistently. (You did usually use “OK.”) “Alright” is forcing itself to become a word, but it still grates on a lot of educated readers. “All right” is still preferred and won’t make a reader stop to grit his/her teeth. So, there are two things wrong with this sentence: “"Are you alright man?" he asked.” The “alright” and there should be a comma before “man”—direct address. You wrote “You now” once where you meant “You know.” But I saw little in this way of mistakes, which, for Literotica, puts you in the upper crust on writing ability.

You seem to be writing American style, not British. If so, it’s “toward,” not “towards,” which is British style.

As far as I could see, you never named your protagonist. This is fine with me—it gives the narration just a bit more “it’s me.” But prepare to be criticized for not naming him. You could always do both. You could find an early opportunity to slip a name in and then dispense with it. Thus, the sentence, “"Are you alright man?" he asked.” could have been rendered, “Are you all right, Jason?” and you’d escape that particular criticism.

You show sensitivity to having a three-month gap between chapters 2 and 3. In Literotica custom this isn’t long at all. But I agree that it’s too long to expect readers to stick with you. I think the best thing by far is to write the whole thing before posting any of it (this, in fact, gives it more chance to be a coherent, trim story) and letting your readers know up front how many chapters it is and when it’s likely to be completed—and then don’t go longer than submitting the next chapter right after the previous one has posted.

A really nice first timer story. I don’t know where you plan on taking it from here, but I think it would be best just to end it here and not spin off into tangents that destroy the “first time” theme. But you’ll always receive the siren song in comments to just keep on writing. To me, that more often than not is writing it into the ground and a grave.