Chapter 9
by
OathkeeperPath
Does this change anything?
Not really, well sort of.
You've found yourself enjoying your time with Seb more and more as things went on. He seemed to be surprised every time you enthusiastically pushed yourself forward anytime an obstacle would get in your way or be mentioned. Despite everything you've done to demonstrate 'I don't quit anything, I just work harder to earn it.'
You'd thought giving him head and putting on your best horny sultry act would have assuaged his doubts but it seems you have a habit of disrupting his views of what you are willing to do to earn what you want.
So far you've not blinked at any of it, not that anything to the scale of first day of fem at the gym or giving head for the first time. Its just been mostly getting used to college in fem and getting into the new gym courses. A few stares and maybe a comment or two isn't a big deal after Dan's out burst.
There's not a single masculine thing left on your side of the dorm and its been slowly getting filled back up with feminine essentials, no decor yet but priorities are what they are.
Mornings consist of shower, hair, moisturize, make-up, meds (not sure why you're still on ankle meds, but you're supposed to finish anything a doc prescribes, right?), bra & panties, run you're outfit by Seb (still working on figuring out what works or not), then breakfast with Seb.
Weekdays are classes and gym time. People seem to be getting used to the new you. You've not run into any of Alice's group but they are all in different courses or class times. Seb goes to hangout with them occasionally but him still being 'friends & roommates' with you has him a bit low on social capital you think. You try to make it up to him any time you start to dwell on it, he doesn't seem to mind how you're conscience is cleared as long as it don't leave him so wore out he can't get up in the morning. Its just been head but, the hands in your hair don't feel like he's enjoying it any less each time.
Weekends are spent shopping and doing 'date' nights. Sometimes something new is brought in but its most just filling out the stuff that's already been covered. Tonight was the first night I would be in a skirt for a date. I was nervous but playing it as excited, mostly cause I was a little, progress always made me happy.
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After a nice movie and dinner, a bit cliche but still a good time with the right person, Seb had seemed nervous.
I couldn't figure out why, things had gone well, he was a great BF and I did everything right as far as I could figure. I don't ask Seb what I did right or wrong anymore as it seems to make him worry about me for some reason, so I trust he will tell me when needed like he promised. Even had a little make out during the movie after I near buried myself in his shirt during the movie's many jump scares, I wasn't as scared as I played but then again everything was an act at this point still. Something about how he smelled made me want to stay in his arms forever and I got a little handsy which lead to the make out. That was real, the first real kiss I'd given him, or anyone else for that matter.
My heart was still fluttering thinking about it later in the night through dinner and the ride home. His flirting and teasing through the night made me flush more than normal and had me curious. He was more into the date with me than normal and now that we made it home he was nervous, it kept me from pushing him on the bed and having my way between his legs.
I sat on my bed instead, trying to show reassuring body language while waiting for his to quit waffling and come out with what ever was bothering him.
"Seb its just me, whatevers got you all stressed you can tell me. And If not I'm sure I can make you forget whats wrong." I end with a wink and smirk I hope comes across right.
He seems to snap out of it but is already on the defensive, "Wrong, who said anything about wrong?" I let him sit with that statement a sec as I give him an incredulous look. "Ok, fine, its not so much wrong as I don't know how to bring it up or say it."
"You know me Seb, you can give it to me straight, I don't need a lot of fluff or whatever to handle something." He smiles a bit to that at first then near laughs.
"Funny you say 'give it to me straight', That's what I was planning to do to you but not sure how to bring THAT up." He's near giggling at this point from nerves I can tell.
"Really funny Seb, I've got no problem doing alot of things to learn how to be a chick, but I'm planning on being with a lesbian, I don't think I need to learn much sex wise from a guy, trans or not, besides giving good head. If you're wanting a turn as the lead during sex then feel free to return the favor, push me on the bed, and try your hand, or mouth, at oral."
"Its not about returning the favor, whose on top, or anything like that. First off I'm not ever giving you head, I'm a straight guy and helping you does not come with a side of dick sucking.-
I cut him off with my best pout and wink, "Never? But I've been such a good girl haven't I? I've not got any release for so long, I assumed I just needed to keep working you harder until you felt I'd earned it, I'm sure you'd look handsome between my legs."
"Ignoring all of that, Well most of that,..." He gets one of those looks on his face again like I've said something 'crazy' like he likes to say, but I can't figure what that might be. "ARE You telling me that you've not gotten off this entire time? No masturbating or anything else? How!?" The way he stressed those words makes him look cute.
"NoPe," I pop the P because I like the way it makes his face scrunch in confusion and frustration when I answer like that.
"Again HOW!? Are you just Ace and haven't figure it out yet?"
"NoooPe," there it is, that one really made his face scrunch up, "Well I'm not going to cheat on you, not very lady like. And I doubt masturbating like a guy is going to do productive. You've not covered how girl masturbate, between that and you not giving me head I assumed you were the type that liked to leave a girl hot and bothered until she begged for it. Was planning to do that soon to be honest, was getting really hard not too, and the dreams I've been having aren't helping."
"Of course," His face starts to go through the five stages a grief, "I keep forgetting how messed up you are." He mutter before trying to get back on track. "And where did you did you get those Ideas from? Nope, don't answer that it was from a porno or movie I'm betting."
At my energetic nod his face seems to have finally landed at acceptance.
"Now I'm just worried about what next crazy thing you'll bring up," Muttering again and shaking his head to clear it and get back on track, I tilt my head in confusion at the crazy comment making another appearance but otherwise let him continue, he is the expert here. "Never mind that, its just borrowing tomorrows problems, back on track. You really do need to need to know more than Oral, Lesbians do more than just that. I can't believe you're 'instructional' porn didn't cover that, who doesn't watch lesbians?"
I go to answer that I wouldn't, as up until this point I'd been trying to be in a hetero relationship so why would I need to know anything from the other categories. I don't though cause the look on his face tells me that was clearly rhetorical and he needed to finish now or may never get it out.
"Lesbian's or at least some of them, wear strap-ons and fuck. That's what I was wanting to talk to you about."
"Well if needed I can wear one over my cock if that's whats needed, seems a bit odd to waste the one I've already got attached tho."
"That's wear the problem is, she is a top, she likes to 'give it' to her partners." He looks at me near squinting like he's looking for something, I've seen others give me that look. When they are expecting me to back down or break.
"Oh? Is that all?" I've never backed down, why start now, "What do I need to do to prepare, I'm assuming its not something you can do out of the blue?"
"Just like that?"
"Yup!" My nerves and fear are making me sound more giddy than I meant to, 'I can work with this', with that thought I crush the nerves down as best I can.
"Do you understand what that means? Not just anal or what ever weird version of reality is going through that cute head of yours, she is very much going to expect her partners to have different plumbing, as in that's a deal breaker."
"So? I'm sure if they can give you a near full functional cock they can give me something that will 'pass inspection'."
"...I can't deal with your crazy anymore. Despite everything I still want to help you, still being horny is not hurting either. Ok you want it? You got it, we are starting tonight. Turn you cute ass around, On the bed slut, ass in the air, I'm going to see if I can't fuck the crazy outta you or fuck some sanity back in."
Its a bit out of pocket as far as dirty talk goes, but with how on edge and horny I've been this whole time his commanding tone has me leaking pre-cum already despite not being hard somehow. I'd taken that as a blessing with the clothes I've been wearing but now I'm about to have sex with it still soft! 'What if he thinks I'm not into it or that I don't appreciate-'
My train of though derails when I feel his hands on me a second later, nails trailing my ass through the leggings he had me wear today. Pleasant shivers run through my up and down my spine as one hand moves up my back. I've never been this horny before, my heart is racing and I'm already breathing like I was at a dead sprint.
"Take the shirt off slut." The tone and words has the hairs on my head tingling. I race to do as asked.
He's already undone my bra by the time I get the shirt off and it comes with. I can feel something poking me through the leggings and panties as his hands move to my chest. I can't believe how much pleasure shoots through me at him treating my nipples as his new favorite toy.
"ooohhu" The first moan escapes mouth and he takes that as permission to get a bit rougher tearing another louder moan from me, "UUUUHHOOOooo."part of me can't believe what I'm letting him do to me. That part is dragged out back and beat by the parts of me that needs this. As a goal for sure, but also I NEED HIM right now, more than ever.
"There's my good girl, going to need to work on how your moans sound, but I'm sure we'll have that down even before the voice training get really going."
I'm having a hard time paying attention to anything he's saying with how on fire my body feels as he keeps playing with me, teasing me, putting me on edge. 'Doesn't he know how on edge I already am!'
With a shift hes now grabbing my chest, "Such a shame your breasts are so small, I'm sure they would be quite something to play with if we worked on getting you a decent pair, wouldn't that be nice slut?"
I moan in agreement, not thinking about anything besides keeping him happy so he will keep playing with me.
"I'm sure you'd love them, your ass is coming along nicely." with the change in subject I feel a light smack hit each cheek get a yelp sound from me each time. "But I'm sure we can make it better when we look into a nice of tits."
Something seems to be changing in him, he's getting more playful and more commanding than I'm used to. I don't really care, where I'm at mentally right now would let him do just about anything. 'God why won't he fuck me yet?!'
My unanswered question gets a response, "Ya know with how you were expecting this to go, I think I want to hear it, you want release. Want me to keep training you and give you my hard cock, I want you to beg for it, beg for it slut."
Oh.
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AN: I'm back from hiatus, lets hope the gods are **** to my schedule moving forward.
Patreon /Kiss_Gemini
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Loving A Lesbian
(Re)New(ed) Plan
You've fallen in love with your best friend, sadly she does not feel the same way and things get awkward. When you find out its because she is into girls the same way you are, it gives you an idea, to fix the friendship you broke, and at least get one date, you enlist the help of your college roommate to help you get feminine. Its not really any crazier than any of your other plans to be truthful. -Doing a Rom-Com this time, sexy scenes will still happen, its still me writing it after all. ;)
Updated on May 2, 2026
by OathkeeperPath
Created on Sep 3, 2024
by OathkeeperPath
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