Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 23 by caitlynmasked caitlynmasked

What's next?

Chapter 22 - Trixie takes Paris home

With a sexy woman draping her buxom body over mine, kissing me, caressing me, and promising to teach me how to be with a woman, how could I possibly say no? Even If the assumption that leads to this fantasy situation, is so SO wrong? Afterall, the assumption is one that I’ve been pushing at the office. It’s one that I have to repeat to my gender therapist. Trixie’s assumption is that I’m a straight woman going through a gender transition because I was born in the wrong body. Yeah, she thinks I’m attracted to men. Yeah, she thinks I’m being stiff and awkward because being with a woman is new to me, not because being SEEN as a woman being with a woman is new to me. Yeah, we’ve bonded over talking about men.

But if living all that means getting to have Trixie ‘teach’ me how to be with a woman? Hell yeah, sign me up! With my mind made up I’m finally able to breathlessly say, “Like, yeah. I’m okay with it Trixie. It’s just, like, you know, a little weird. But good weird! Fun weird!”

Trixie’s return grin says everything I need to know. That she’s going to enjoy teaching the ‘innocent’ girl how to make love to another girl.

Trixie continues to kiss and pet me all throughout our bottle of wine. She seems to love slowly rubbing over my smooth skin, telling me in her sultry whispered voice how sexy it feels to have smooth skin touching smooth skin. How a more gentle touch is just as exciting as a big strong man’s touch. How her soft kisses are as good as a man’s more aggressive kisses. Her smooth cheek against mine vs a man’s stubble or beard. Her satin covered thigh rubbing over my silk covered one.

By the time our bottle and glasses are empty I feel like I’m about to pop. I’m so hard under my gaff that I’m half afraid I’ll rip both it and my panties when I stand up. This achy arousal is something I’ve never experienced before and leaves me breathless as Trixie takes my hand and guides us out of the bar.

I don’t question even once where she’s taking me when we get to the station and Trixie doesn’t give me a chance to gather my thoughts on the train. As soon as we find a couple seats together, we sit down and she picks right up where she left off, brushing my hair back and kissing at my neck, jaw, and ear. When I get the gumption to open my eyes, I see that we’re making quite the spectacle, but putting on a show for these people is a price worth paying to have Trixie make me feel this good.

We take the blue line up to Damen Ave. It’s not a long walk from there to Trixie’s Bucktown apartment. Before she even unlocks her door, I find myself pressed up against it, Trixie’s thigh pressed between mine and rubbing up and down as she cups my head in her hands and presses our lips together.

This entire situation is both completely foreign and at the same time familiar. I’ve never been handled like this before. Never been the passive one in kissing and making out. I’m used to leading the ladies, kissing them, letting them know how to please me. But here I am, pressed up against Trixie’s door as she pulls my wrist so that I cup her ass while moaning into her ever kissing mouth as she rubs her thigh between my legs. And while a part of me believes this works to my advantage, that being the shy ‘this is new to me’ girl works for Trixie wanting to ‘teach’ me, it’s not as though this was a plan I laid out. I couldn’t have been this out of touch and nervous if I’d tried. Every move I make, I’m surrounded by the silks and satins that I’m wearing. The slight breeze up my skirt reminds me of my stockings covering my hairless legs. Trixie’s hand cupping my breasts, moving the little plastic tongues over my nipple keeps driving me mad. Even the smells overwhelm me. It’s not Trixie’s or my individual perfumes, it’s the heady combination of the two leaving no room for the normal masculine scent I’m used to. I never once thought I’d miss smelling like a man!

I nearly fall back onto my padded ass when Trixie unlocks the door and slips it open behind me. When I catch my balance, I find myself shifted backward into Trixie’s living room, my butt butted up against the back of her couch. My breath catches in my throat as I watch Trixie stalk in after me. Her eyes never leave me and have the look of a slowly approaching predator. The door closes and locks behind her, but I barely notice as she starts by dropping her coat and purse and immediately starts slipping out of her blouse and wiggling out of her skin tight skirt. By the time she presses up against me again she’s wearing only a bra, her panties, and a pair of nude pantyhose.

I’m not sure exactly what I was going to say but the words escape me when Trixie again attacks my neck with her kisses and all I can do is moan my appreciation. One of my hands finds its way to her satiny smooth ass while the other cups her lacy bra covered breast. When Trixie’s mouth makes its way up to my cheek, I just assume she’s headed to my earlobe again with my toes curling in anticipation. Instead, however, she changes direction, and we enter into another lip lock. I feed Trixie a muffled surprised cry when she gathers up a handful of my hair and grips it tightly.

When she breaks the kiss, I don’t have time to even ask what she’s doing as she uses my hair as a handle and guides my face down to her breast. She must have reached around behind herself with her other hand as her bra falls between us leaving my lips and tongue open access to her diamond hard nipple which she guides to my warm mouth. While I start suckling at this beautiful woman I hear her voice float down, filled with sultry breathless overtones of pleasure, “I know you like being with strong men Paris. To help, I’ll play that part for you. Just follow my lead like you would your man. And don’t worry baby, while you’ll be pleasing me first you won’t, like, get to leave until you’ve screamed from your first sapphic orgasm!”

Trixie’s combination of sultry, commanding, and bimboesque tones is heady but easy to comply with as she keeps me latched to her nipple and walks us around to the other side of the couch. As Trixie lays back on the couch, propping her head up on one arm and spreading her legs out wide, she leads me to lay down between her glorious thighs. While both of her hands gather up my hair and start directing me from one breast to the other, her little squealing moans of pleasure floating around me, I start rubbing and caressing her lovely pale flesh wherever I can touch it.

For what feels like the next twenty years, but is likely only twenty minutes, Trixie treats my tongue and lips like a set of toys ushering me from one erogenous zone to the next. Nipple to nipple, the underside of her breast to her neck, her lips to her earlobe, back between her breasts and down to her belly. All the while I feel as though I’m going to explode out of my panties. Between my gaffe, my panties, my skirt, and just the position I’m in, I have no leverage to even dry hump one of Trixie’s legs or the couch itself, leaving me to just throb in unresolved, unrelenting, unrealized pleasure.

I recall Grace once telling me how sex to her is all about the buildup. That what I consider foreplay is her main event that she makes last as long as possible, and that the orgasm is almost a let down as it ends so comparatively quickly. And as I finally am directed down to Trixie’s wet and musky pussy… when did she slide her pantyhose and panties down?... I wonder if I’d be able to stand a steady diet of sex like this. At this point I recognize that I’m near mad with lust and would do almost anything for that sweet release. At the same time, while orgasms certainly feel better than this, I’ve never had one last more than a few seconds and this sensation has lasted at least three different eternities.

When I’m finally able to lick up and taste Trixie’s nectar I feel that I’m able to take at least a semblance of control. I vastly prefer women performing oral on me, but some chicks are prudes and won’t go down unless I go down on them first. So, I’ve more than learned my way around pleasing a woman with my mouth. But while I bring out my A game, Trixie shifts and huffs with less than the full pleasure I expected. Her words, though whispered in a friendly, loving, earnest tone, cuts me to the core, “Mmm… don’t worry baby I know licking cunny is new. I’ll, like, teach you how to make a girl feel as good as when you suck cock!”

My hardon doesn’t go down one little bit for the next thirty minutes, though I feel like a freshman being overwhelmed in a senior level class. All I can think is that those poor girls that I’d licked before either hadn’t ever been eaten out properly or were the best damn liars I’d ever heard scream out in ecstasy. Trixie is a patient plodding teacher, telling me how to curl and flatten my tongue for different sensations. How to use my saliva and her juices to make everything sloppy and wet and then how to lap it all up, swallow it down, and start over. She taught me how to lick and kiss. How to use my lips, my tongue, my teeth, my nose, and even my chin on different areas of her pussy to bring her differing levels and types of pleasure. And while I was frustrated and hurt at first, by the end of Trixie’s master class on cunnilingus, I feel like I could write my own thesis on the subject.

And yet, even after Trixie squeals out her high pitched cries of pleasure while clenching my face between her muscular yet plush thighs, even after I drag out her orgasm as long as I can, she still hits me where it hurts by petting my hair and telling me, “That was nice Paris… you’ll be really good one day at making a girl feel, ya know, good if you keep working at it!”

Any pretense I have of being hurt by Trixie’s words though are erased as she props me up and starts undressing me. While she takes some time to admire my faja, and especially notices that I can feel when she moves my breasts or jiggles my rear, she doesn’t slow down until I’m down to my panties, garter belt, and stockings. When she lays me back, reversing our positions on the couch with my head resting on the arm and her crawling between my spread legs, she clucks her tongue at me, “Tsk tsk tsk, you should know better than this sweety! Wear your panties over your garter so it’s easier to take them off and leave your stockings on. I know your guys love to see you in just your belt and hose, but us ladies like that too!”

I’m more than a little surprised when Trixie reaches under the couch and comes up with a pair of clothing shears. Without waiting for permission or asking for it, she deftly slides the scissors under the thinner area of my panties and gaff and with two simple cuts is able to slip my ruined underclothes out from under me and toss them across the apartment. A part of me feels like I should complain as gaffs aren’t exactly available everywhere, but as my cock flips out and throbs as it’s blood flow grows unrestricted, I relax back and decide this isn’t the time to care about such minutia.

Trixie hums and makes appreciative noises as she starts to kiss her way around my hairless thighs. Her area to kiss, compared to the work area I had between her legs, is limited by my faja, but she still takes her time and seems to treat my cock as almost an afterthought. She kisses and licks at my thighs. She nibbles at and flicks my ball sack with her tongue. She grips my cock by the lower shaft and holds it out of the way while she kisses and rubs her nose just above it. For minutes I can only wiggle and moan and mewl under her attention. I thought I was on edge before, but somehow Trixie is able to amp up my pleasure up without taking me over the edge.

Even when she acknowledges the presence of my cock and starts working on it in earnest, it’s in a teasing almost denying manner. With a single finger under the cockhead, she holds my hardness up against my body and then assaults my shaft with little licks and kisses absolutely everywhere that she can reach. Just as I feel I’m going to burst she lets go, letting my cock rocket straight up and just throb in the air, as she moves back to lick and suckle on my balls.

I must have licked and worked at Trixie’s pussy for a half hour. Her return favor is to lick and kiss and tease me for a full forty-five minutes. Whenever I try to reach for her, to just pet her hair or guide her to where I want her attention, she easily guides my hands elsewhere. To her arms, or my legs, or even once under my back.

Just when I don’t think I can take any more, when a mere breath of hers will send me over the edge, Trixie overwhelms me with a single wet flat lick to the underside of my cockhead. Her hands grip my waist and hold me down as I begin to thrash and erupt streams of cum with nothing but the tip of her tongue barely flicking across the underside of my cock.

When I’m finally spent and fall limp back into the couch, Trixie climbs up me and turns us so we’re lying side by side. With barely enough room, I find myself taking deep breaths trying to catch up on all the oxygen I just screamed out while staring into Trixie’s beautiful eyes. I can only nod in appreciation as I listen to her whispered, quiet voice, “That’s the closest you’ll have to a girly orgasm until the hormones change you sweety. And you should, like, ONLY have big Os like that from now on. Promise me…” she leans forward and kisses me gently on my lips and the tip of my nose “…promise me that you won’t pleasure yourself like a man. That you’ll only cum like that from now on. Cum like a good girl from now on!”

What's next?

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)