I roll over, back under my sheets right after I read her promissory message. I changed back into boxers in a fit of shame after coming home last night. Still the thrill of that night lingers like a lead weight on my chest, making my breathing shallow and constricted. The sensation resurrects the memory of her hand holding me down against the mattress, the sharpness of her narrowed, blue leer pinning me to the sheets like a silver needle. “Fuck,” I pant, tossing the sheets off of my shoulders and over to the foot of the bed.
My swelling arousal confesses what my thoughts cannot. I don’t dare let it bleed into words, even as a faint inkling of cognition. I need to see her again. I need more.
I make an effort to spend my morning as normally as possible. I turn on the television while I make breakfast, hoping that the little whispers of desire accumulating in my head would be replaced by some monotonous morning show. It’s no use. Every word floats through my mind on a flood of yearning, dissolving in my hands before I can gather enough pieces to form a single clause.
*It was just a one time thing* I try to assure myself.
I flip to the news as my pancakes sizzle in the skillet. The anchor drones on about oil prices and disagreements between fossil fuel oligarchs. Nothing to even get mad about, at least any more than the residual frustration that accompanies current affairs. After a few minutes the words stop, replaced by a steady tempo of indiscernible nonsense. The image of Florence’s pale figure shifting in long, winding waves over my body crashes into my consciousness. All other considerations are washed away as the tide draws back.
My phone slips out of my pocket, my fingers hit keys, and I cannot think about what I’m doing. Florence’s name comes up in a header, followed by her number. I begin typing. *I had a lot of fun. I’d love to do it again sometime.* I place my phone down on the counter and grab a spatula to save my burning breakfast.
The response is almost instant. *Great. I’m getting a surprise for you. A few surprises actually. I can’t wait for you to see them.* She dots the end of her text with a winking emoji.
We text back and forth until morning draws into afternoon. Finally she gets tired of waiting. A new message pops onto my screen. *Come over.*
*Now?* I send back.
*Now* she demands.
In a matter of minutes I’m knocking on her door. “Come on in,” she calls, her voice accompanied by a flurry of footsteps. She greets me in her underwear, a lacy set of black lingerie, and drags me across the threshold by the collar of my shirt.
“I’ve been so excited to see you again,” she confesses. “So, what are you wearing under there?”
“Nothing,” I admit before lowering my tone, “Just boxers.”
“Really?” Her brows can’t hide a disappointed pout. “I guess it doesn’t really matter. In fact, that brings me nicely to my surprises.”
I get antsy, “Look, I just.” I pause, doubting myself. “I just don’t know if I should be doing this.”
She wraps her arms around the small of my back. “No, no, I promise it’s okay. What’s wrong? Do you feel guilty?”
“I-” I stumble, “Yeah, yes. I feel kinda weird about the whole thing. Like I’m doing something wrong.”
“You’re not doing anything wrong,” she promises, drawing me in for a hug. “There’s nothing wrong with liking this. You’re not hurting anyone. You’re just doing something you enjoy. Maybe it’s a little different from what other people like, but that’s the way all good things are.” I gather my arms around her and rest my head on her shoulder. I draw in a ragged breath and sigh.
“Thanks,” I whisper. “I don’t know why, I just really needed that. I really need this too, what we’re about to do, I mean.” She gives my back an assuring rub. I bring my head up to look at her face. She smiles at me through ruby lipstick.
“So are you feeling up for a little makeup?” she asks before running her fingers through my hair.
“What about the surprise you were talking about?” I regain my composure.
“I can show you after,” she says, “I think it’ll be more fun to have the whole package at once.”
She escorts me over to her bathroom again and tells me to disrobe before getting to work on me with a full arsenal of brushes and sponges. Once more I’m transfigured in concealer and contour, primer and blush, eyeliner and mascara.
“Good?” her voice chimes. I nod timidly at my feminine reflection.
“Good.”
“Great. Now for the surprise.” Her voice turns jovial as she walks out of the bathroom and over to her closet. She returns with a tall gift bag. She casts her arm into the shoots of soft pink tissue paper, drawing out sheer blue bralette. “I did my best on the size, but I think it’ll fit you pretty snugly.” I eagerly take it over my shoulders before modeling it in the mirror.
She giggles at my enthusiasm before picking a matching thong out of the bag. I reach over to take it from her but she stops me. “There’s one little thing I want to try on you before you put this on.” He hand goes back in the bag to bob for the last item. A small, velvet bag emerges. She loosens the cord and pulls out a pair of small objects. “Do you know what this is?”
I shake my head.
“This is a chastity cage,” she explains, inflecting heavily on the first note. “It makes sure good little sluts like you stay sweet and submissive.” She softly kisses my cheek. “So do you want to try it out?”
I let out a meek, hesitant “Yes.”
“Only if you want to.”
“I want to.”
Without another word she slides the cool metallic ring over my balls before tucking my limp cock into it. “Try not to get hard,” she says as my shaft twitches and flexes. She slides the second piece of the entirety of my member before fastening the lock into place. Finally she turns the key, before fixing to a string and letting it dangle over her chest as a necklace. She gives me the blue panties to put on after toying with the cage for a moment.
“I can already tell you’re going to make such a good little whore,” she whispers, admiring the obedient girl she’s already made of me. “So here’s what we’re going to do. I’m going to get one of my toys and we’re going to give you a little training. If you’re really good for me, then tomorrow I’ll let you out and I’ll use my mouth to give you exactly what you need. Does that sound good?”
I swallow heavily and nod. “Yes, mistress.”
Source: reddit.com/r/eroticliterature/comments/ge01qj/crossdressing_confessions_part_iv