Crossdressing Confessions Ch. 05

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My face is pressed closely to her sheets, my blush-covered cheeks just faintly grazing her white-cream toned sheets. I can feel her stalking behind me, creeping closer and closer with a predatory sense of pleasure. She is like a snake on the verge of striking, and I am her prey. I feel like a trembling, thoughtless mass of warmth just waiting to be constricted.

“How about we make this a little more interesting,” Florence muses, as though she hasn’t already launched a full fleet of surprises. She drags a solitary nail up and down my back, before correcting my position. I can feel the smooth, glossy finish on her nail as she traces the proper arch of my back. The sensation creates a feeling of weight bearing down on my own painted fingers and toes. The shallow hue of pink is sinking into me, pressuring my hands deeper into the mattress.

“Legs apart,” Florence orders. I obey. “Keep your face down. Don’t stop bending your back. You’re trying to show off your ass and nothing else. More. Relax your feet. Good.” She does some manhandling to make adjustments. “Perfect. Now hold still.”

She goes to get a toy from her closet, but I can’t see what it is. “Are you ready? We’re going to start with something small and then we’ll work our way up. It’ll only be a matter of time before you’re begging for my biggest toys.”

“Yeah, I think I’m good.”

“How many times am I going to have to remind you of the proper way of addressing your mistress?” Her tone is more teasing than scolding. “Try again.”

“Sorry,” I whisper, before obliging more loudly, “Yes mistress.”

“Better.” I feel my panties slide down to my knees. A sense of defenselessness overwhelms me, bringing an icy shiver spasming down my spine. She takes my cage between two fingers and jostles it back and forth, making the lock rattle. My member swells only to be stopped by tight plastic walls. It aches sex hikayeleri with the phantom sensation of her touch. The struggle gives the lock another delicate shake.

“You really want it, don’t you?” Her smirk is audible in her tone. “You just want me to let you out of your little cage. You want me to stroke your little cock. Maybe you want to cum all over my perfect tits. Or maybe you want to finish in my throat and watch my swallow.”

She pauses as I tremble with anticipation and the imagination runs wild. “But that’s not going to happen now, is it? You’re not my master and I’m not your dirty little girl. I’m your mistress and you’re going to be obey me like the submissive slut that you are. As long as we’re in this room, you belong to me.”

I don’t say anything. “Is that clear?” she presses.

“Yes mistress.”


Something smooth and hard enters me. I gasp as the first little micrometer successfully penetrates me. I don’t have time to recover before it’s shoved deeper inside me, and my gasp transforms into a moan. A strange sense of completeness unfurls inside of me.

“I can’t wait to see how you react to the bigger ones,” she murmurs as she withdraws. She takes things slowly, gradually pushing in and out of my ass with her dildo. I writhe as she makes the second push. A wave of motion travels down my back and echoes down my arms. I lose my grip on her sheets and my face plunges deeper into her sheets. My knees slide further to either side. My hands grope around the bed before clawing onto the bundled sheets once again. My face rises from the surface of the bed.

She pulls out. “Back in position. Face down, ass up.” I do my best to recompose myself. Face down. Arms to the sides. Back arched. Ass up.

“Not bad. Bring your ass up higher.” Her plastic shaft enters me again after I comply. I bury a whimper with porno hikayeleri teeth pressed harshly into my lower lip. She thrusts the toy deeper, pushing further and further until I feel its base slap against my ass. She shakes it slightly. The tender friction spreads throughout my asshole. The small, deep motions continue before she pulls out once again. I tremble, this time mindful not to lose my position.

“So what do you think? Do you want to try a bigger one or are you done?”

“I think I need a break for a minute,” I sputter.

“Sure,” she says with casual indifference. “Turn over, I’ll take care of you.”

I slump over to my side, making a light thump as my butt slams against the bed. Florence slithers up next to me and pets my cheek. “Are you okay?”

“Yeah,” I say, “It was just a lot.”

“You’ll get used to it,” she rests another hand on my neck as she continues petting me. “I mean if you want to do it again, that is.” She leans in and kisses my forehead, transferring a sense of calm with the affectionate peck. “We can take things a little easier if you want.”

“No, no,” I insist, “I liked it. Something about it was really satisfying actually. I felt sort of complete, you know?”

She smiles at me, but it also strikes me that she’s marveling at me somehow. I wonder if she has the same expression when she watches the first brilliant wing break out of a chrysalis. I feel different in a way I can’t put into words.

“Sorry, that was kind of stupid.”

“No, it’s not,” she assures me, “I’m just glad you’re enjoying yourself.” She kisses me again, this time on the cheek. “Which is good, because you make a really cute girl.” I blush under my makeup. A genuine sense of flattery stems from her comment. It makes me proud, but that feeling of pride only makes me feel more shame a moment later. She holds me. I have no idea for seks hikayeleri how long, I lose myself in her comfort.

“Ready to go again?” she asks, sending me stumbling back into time.

“Yeah, I think so.”

“Cutie,” she grins, “You can stay where you are, just pull your legs up.” She grabs her strap-on, replacing her first instrument with a slightly larger one as I arrange myself. In a matter of moments, she’s towering over me. After applying a healthy dose of lube, she starts again. I feel the increase of girth immediately. The tight ring of my asshole struggles against the dildo for a brief moment before surrendering. I feel it open wider to allow the entire plastic shaft inside of me.

She builds up speed this time, starting with the same gentle rhythm as the first toy before hitting her stride. Her lips pressed into mine, partially muting me just as a whimper escaped. She takes my hands in hers and forces them down as her toy continues to work more and more eagerly. “You’re such a good little slut, aren’t you?”

I can only admit a whine in response as she keeps fucking me. My face is burning up in a frenzied tide of blush. My lips contort, forming silent o’s and f’s. “Yes mistress. I’m you’re good little slut. I’m your little whore.”

She doesn’t relent until my flaccid cock twitches and trembles as my whole body lights up in an unfamiliar, but orgasmic surge. A tiny sliver of white cum trickles from the head of my cock, leaking down along the outside of my cage.

Florence takes on an amused look. “I didn’t see that coming. Here, you’ve earned this.” She brings her face down to my groin and drags her tongue along the surface of the cage. She lets the cum linger on her tongue long enough to bring her head up and show me. I watch wide-eyed as she swallows. “You’re lucky I’m such a bad mistress. I should have had you clean yourself up.”

“It’s still the same deal as before,” she continues, “Keep it on until tomorrow and I’ll give you a blowjob. If you wear your panties too, then I’ll swallow again. Is that fair?”

“It’s a deal,” I say, before adding “mistress” with a sly look.

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