The Cute Boi and the Shemale [EAENIDU]

[Kuragari]

Name: Angel Summers
Gender: Male
Appearance: https://steamuserimages-a.akamaihd.net/ugc/1834665852181707690/F52F97D2F1EDBDE17D62BB8D4BE2E97C36040DAE/
Bio: Angel has always been, well... a good boy. Doing what he's told following rules, whatever. Recently though Angel has finally moved out to live on his own to attend college as well as working on writing some having always liked the idea of being a writer. Where he was studying to get a Liberal Arts Degree as well as minoring in "Gender Studies" mostly because he found himself interested. When as part of the course he had to dress for a day in "Traditionally Female Clothing" he found it...oddly freeing and making him feel better about himself. Interested he bought some things and walked around his house dressed as a girl and found that he liked it a lot. Finally one day he decided to go for a walk dressed as a girl. Only to get scared as he realized some men were following him. Running away he stumbled into a woman and quickly begged for her help in a panic. He didn't even question when she quickly took him inside a building and followed her without a second thought into her apartment.

You were pulled into her complex, and hurried up to her room. Your head was spinning from an enticing scent wafting off her as your heart raced from the fear from those big men that had been tailing you. As you were brought into her apartment, the sexy, pretty woman softly ran her hand soothing through your hair while the other massaged gently at your shoulder. After a moment, she asked, to your surprise,

"First time out and crossdressing ey cutie~?"

Spoiler (click to show/hide):

Am at work so don't have access to being able to find a good pic for the shemale, so I'll let you choose one or come up with a few

[eaenidu]

I was panting a bit and trying to calm down while she pet me, which felt weirdly relaxing making me lean into her hand a bit, only to squeak and jump at the first words she said "H~How did you?" I asked with a blush, then thought and tried to quickly stammer out "I~I'm not a pervert O~Or anything...I~I'm taking a Minor in Gender Studies, I~I was supposed to dress like a girl, and." I squeaked again covering my face "I~I'm, It, It just felt...right, and, and I wanted to go out, not just in my room, B~But I wasn't expecting guys to actually follow me or anything I~I was scared for real!" I admitted finally looking at her through my fingers.

[Kuragari]

"Mhm, relax cutie. Even if you weren't doing it for a class, I wouldn't judge you. After all, why judge when we're so similar." She says as she pulls you against her more, still petting your hair and massaging your shoulders. But you feel two things that leave your head conflicted. First, you feel the swelling of her chest, which feels nice and soft and plump.

But then, against your ass, you feel a bulge through her lower garments. Something that feels hard and hot and makes your brain cross as it tries to briefly figure out what's going on before doing just that and realizing it wasn't some ordinary woman who'd saved you.

[eaenidu]

I Blushed and wiggled "O~OH, W~What Am I supposed to do then?" I asked only to squeak and wiggle unsure with what was happening, it took me a few seconds to realize that the odd feeling on my ass was her cock getting hard and rubbing my ass making me flush even more, it felt...nice.

[Kuragari]

Spoiler (click to show/hide):

https://cdn.discordapp.com/attachments/855623953610178572/977545839398494208/unknown.png the shemale

She smirks as she peers down at you from above, her hands now moving to slide up and down along your sides, giving your ass a grope here and there as she ground her own hardon through her form fitting shorts.

"That'd be up to you sweetie. I saved you because you looked like a cutie in need of rescue. But what you do next... mhm, well, you could go on off on your way, or just have a friendly chat with someone whose been in your shoes before..."

She pressed you back into her again, her breasts against your head and her bulge poking the base of your spine. "Or if you were up for it... we could do something a bit more fun~"

[eaenidu]

I squeaked then blushed brightly. I'd never got any attention from girls before, I was always seen as "One of the Gals" even. It was pretty embarrassing to have her grind against me like this, the groping as well soon had me practically glowing red and wiggling in her lap.

When she made her offers...I found I didn't want to leave, still a little afraid of going out, I blushed more as she pulled me back into her embrace tighter, and told me the other option though "I~I don't wanna go out yet. B~But I've never done...Anything, like that..." maybe I should just talk for a bit, but she felt really hard...
((3))
I Blushed more and looked up at her "Y~You're really pretty, am, am I really making you that hard?" I murmured blushing as I wiggled my but against her bulge "U~Um, W~Well, Y~You did help me..." I trailed off grinding again her shaft "W~Well I mean I guess I could try out being the girl for you..." I murmured leaning into the larger...man's? Woman's? Grip and shyly looking up at her "J~Just tell me what to do~?" I stuttered out with a pretty blush.

[Kuragari]

Smirking, she guided you over to a couch nearby, and soon enough gently pushed you into it. She then slid to her knees in front of you, spreading your legs as she said, "Right now? Just relax, and let me help you enjoy yourself a bit... then you can give me some relief too~"

[eaenidu]

I squeaked and blushed at the very pretty person kneeling in front of me, looking at my own hard cock, I felt really embarrassed because while I was wearing a skirt and a cute top, I was also wearing panties which she could easily see...they were cute white and pink striped panties with a pink bow pretty much right where my cock head was pressed against...the other embarrassing thing was the fact that her bulge felt bigger than my fully hard cock, but even as embarrassed as I was, I just stared at her and submissively let her guide me into whatever position she wanted me in.

[Kuragari]

Smirking, she relieves you of your panties, setting them aside as she sizes up your dick. "A bit above average. Not bad. The question of course is, does it taste good~?" She leans in, taking a breathe of you first before she begins to pepper and plant kisses up and down your pillar, soon moving to flick her tongue this way and that around your cockhead as she wraps her lips around the very tip, where pre is beginning to bead.

[eaenidu]

I let out another squeak, then gasped and moaned at the same time making an odd sound as someone besides me finally touched my penis. and with her lips! and then tongue~! My hips jerked a bit in surprised pleasure "O~Oh~?" I murmured wide eyed unsure of what else to do or say at the feeling, only whimpering in pleasure as her lips wrapped around it.

[Kuragari]

She chuckles, smirking around your cock head as she takes the whole thing into her mouth and begins to suckle on it a bit. Her hand moves to start toying with your orbs as well, though a finger snakes down to give a playful caress at your taint as well as her eyes gleam with sensual mischief.

[eaenidu]

My mouth could only make moans, grunts and gasps...to be honest I was trying to not cum right away, I hadn't jacked off for a couple weeks, mostly due to having to much school work and being to tired, so I was panting and moaning, unable to help myself staring down at her with wide eyed wonder as she teased my no longer virgin body.

[Kuragari]

She pulled back a bit, bringing her finger back up as she made a bit of a lewd show licking and sucking at it. Then she went back to wrapping her lips around your quivering pillar, taking it to the base with ease and letting her throat cling to you briefly as her slickened digit moved to try probing into your backdoor. All while her eyes remained focused on your face, seeming to be enjoying the look you were sporting and the sounds you were making.

[eaenidu]

((2))
I looked down whining in soft confusion as she pulled back, shaking my hips at her needily wondering why she stopped, only to suddenly hear a moan that sounded like it was right from a porno when she swallowed me to the base. Then I felt her finger suddenly poke and prod only to push into me, making my eyes go wide and crossed for a moment while I moaned like a whore and came harder than I ever had in my life, my cock firing shot after shot of cum down her throat as I practically emptied all my backed up jizz all at once and slumped back, my brain hiccupping and shutting down as my eyes rolled up.

[Kuragari]

When you wake back up, your still on her couch. Still pantiless and with your cock out, though its softer now. But there's also a pile of pictures in your lap, of you in various kinds of lewd poses.

"I've got them saved on the cloud, my computer, and my phone~" She singsongs from a recliner nearby, her own cock out and hard as she idly stroked at it, puffing from an electronic cigarette as she smiled at you. "If you don't want me spreading them around, you'll be sure to be a good girly boi for me, got it~?"

[eaenidu]

I took a few seconds looking at the pictures, squeaking at how lewd they were. Then I heard the shemale's voice and looked up seeing her stroke a cock that, if mine was "Above Average" he's could only be called "Big" if not "Huge". Then my brain caught on to the fact that she had the pics saved, then I heard the rest of her statement and squeaked again. Wide eyed in fear, looking down at the pictures then back up at her I could only gulp and nod, "O~Okay, um, Mistress or some O~Other name then?" I said submissively ducking my head "I~I'll be a good girl?" I stutter out, still confused and shocked but obeying.

[Kuragari]

"Mhm, Mistress is perfect, and you catch on right quick~" She smiles as she spreads her legs a bit, letting you see her sac which is twice the size of your own. "A girl is what you shall be when you are spending your time with me. You will dress and act like one, and if needed, I'll help give pointers and tips to make you an expert at crossdressing before too long~"

"But in exchange for me keeping these pics to myself... you'll do exactly as told, and be a good, obedient girl for me. And the first thing I'd like you to do... mhm, is use those soft, cute hands and those precious lips of yours on my pillar. Fair is fair after all~"

[eaenidu]

I squeaked, and stared my brain taking a couple seconds to figure out what to do as I stared wide eyed...before submissively crawling off the couch and over to her on all fours, leaning forwards to kiss her sack, blushing brightly in embarrassment I didn't have a choice! I look up to her face, licking her balls "Y~Yes mistress~" I managed to stutter out...if I just copied her she'd probably think I was lazy? Right? So I decided to suck and worship her balls with my mouth and tongue while jacking her off, even as pretty much my whole body turned red with embarrassment.

[Kuragari]

She watched you crawl over with an appreciative eye, and hummed as she let go of her member to let you start to stroke at it as you tasted her sack. Her balls were salty, likely from sweat, and her scent was making your head spin. She seemed content to watch you for now as you felt your hand grow slick with pre, the feeling of her own cock in your hand and it so close to your face serving as bigger reminders of the difference in size between you both.

[eaenidu]

I blushed as she looked down at my, my brain felt like it was getting smothered with her scent, it was that strong, blushing and jacking her off even as her pre coated my hands I realized just how big she was compared to me...she was easily twice as big and just proved more and more that, even if she had tits I was more of a girl than her...blushing as I realized that soon enough I had licked, kissed and sucked her balls completely clean I thought on what to do next...I could suck her off...or I could try and throw her off balance, instead of leaning up I leaned down, her balls resting on my face, then my eyes as I kissed and licked first her taint, then moved to Rim her while jacking her off, I couldn't see what what happening but maybe I could shock her into cumming quickly?