I start to make my escape but Florence lays a hand on my chest and presses me back into the couch. She looks directly at me and I cannot turn away.
“Yes,” I confess, barely audibly. I try to rise from my seat again but she stops me once more. A capricious spirit takes over her expression. Her eyes narrow and the ends of her mouth curl.
“Don’t worry,” she says “I’m not judging. I kind of like it actually.” I exhale reflexively. She gives me a moment to collect myself. I suspect she is also reevaluating our current arrangement. “Take your clothes off. I want to see.” My cheeks flood with blush at the order, but I comply.
I get to my feet and make short work of my jeans. They’re tight enough on my figure that they come inside out by the time they’re under my ankles. I bend over to fix it but another command interrupts me. “Take your shirt off too. I think I want to know if you’re wearing a bra.”
Leaving my jeans bunched on the floor, I unbutton my shirt and shake it off my shoulders. The sleeves gradually drift from my arms and join my pants down on the ground. I’m wearing nothing but a red pair of panties. With each spasm of breath I take in a miasma of thrill and vulnerability. I feel like a rabbit being stalked by a coyote. Perhaps a butterfly about to be stuck with a pin would be a more fitting metaphor.
“Aren’t you so precious?” Florence muses, looking over my cleanly shaven body as though she’s a tailor taking measurements for a dress. I don’t respond. All I can think to do is put my hands in front of my pelvis, and cling to the hopeless fiction of preserving my masculinity. “Do you know your bra size?” she asks as she gently kneads my chest in her palm.
“No,” I answer honestly.
“That’s a shame. I doubt we’re the same size but I thought I might as well check.” She hesitates, taking time to mull over the first thing she wants to do with her new toy.
“Come upstairs,” she smirks, “let’s do your makeup.”
Within an hour I’m transformed in a flurry of foundation, eyeliner, and lipstick. Florence brings me to her bathroom mirror to show me her handiwork. It’s more like looking at a picture than looking in a mirror. The photographic longing returns, this time satisfied by the transformation of image to mirror.
Florence steps out of the room as I admire my newfound beauty. She returns a moment later with a bra in hand. It’s red, maybe a shade or two off from my underwear. She places the cups over my chest before pulling the straps behind my back.
“Not quite,” she murmurs before tossing the article on the bathroom counter. “You still make a cute girl.”
“Thanks. You did a nice job with it.”
“Thanks,” she brings her arms around me in a hug just over my waist before burying her face in the nape of my neck. She leaves a trail of hot kisses leading up to the corner of my jaw. “Would you be willing to do one more little thing while we’re doing this?”
“Go ahead and ask.”
“Would you be alright with calling me mistress?” she asks. A jolt of anxious excitement kicks through my heart.
“Yeah, sure,” I consent.
“Try again,” she teases.
“What?”
“I think you meant to say ‘Yes, mistress.'” She smirks with self-satisfaction.
“Yes, mistress.”
“Now get in bed and I’ll show you my underwear” she promises, already pulling her dress up to her ribs. She slings her dress over her towel rack and gives me another kiss as I head out the bathroom door.
I toss myself down on the bed as my now-mistress instructed. Her slender figure lingers in the frame of the door. She is almost a silhouette, locked in a poised pose, watching the arousal swell in my flirtatious, lace panties.
She struts over with an aura that demands worship before climbing in bed. She brings her face inches from mine, close enough that I can feel to caress of her breathing. Her fingers reach down to play with the edge of my underwear, pulling and tugging while her other fan explored along my ribcage. She stops to pull of her own underwear and toss it on the floor. Before they hit to floor she pulls my panties down around my knees.
“This is your reward for being such a good girl,” she whispers as she lowers herself onto my shaft. I gasp as she takes the last inch of my member inside of her. Every nerve is consumed by her warmth. My teeth dig into my lips as she bobs her hips up and down, smoothly weaving my cock in and out of her pussy. I push into her in a steady rhythm, digging my hand into her black bra-clad breast and wandering the slender contours of her back. We kiss again as she continues to ride me. Her tongue pierces into my mouth, feeling along the roof of my mouth. Her soft, breathless moans linger in the air as she moves faster and faster.
My cock starts to tremble inside of her, growing warm and red with tension. She grins in response, picking up the pace and pushing me down against the bed with domineering fury. The pressure keeps building as she buries her head in my neck again, this time working her way down along my clavicle.
“Mmm,” she sighs while I shutter with pleasure. I can’t hold myself back any further. My cock erupts in her tender heat, delivering wave after wave of tension followed by release.
“Good girl,” she whispers as I ride the final wave to its conclusion.
“Thank you, mistress,” issues automatically from my lips. She retires to my side, running her nail along the center of my chest in a small circle.
We whisper sweet nothings for a few minutes before falling silent and letting the darkness of the night settle in. I wait an hour before I’m certain she’s asleep. I get out of bed and recover my clothes before shuffling out the door.
My phone buzzes the next morning. *I hope you had fun last night. I know I did.*
Source: reddit.com/r/eroticliterature/comments/gcllp2/crossdressing_confessions_part_iii