So, it was taking over my life - the sissy thing, I mean. I thought I was a regular straight guy and then...well, you know, the usual...porn...then bbc porn...then sissy hypno...then tumblr...it was just a kink, right?
Before long, I had a suitcase full of the sluttiest clothes I could think of, and a few pairs of 5 inch heels that only a stripper could walk in, a chastity cage, various toys...and then one day, in the middle of berating myself for these thoughts an thinking of starting a purge, I shaved. I shaved everything off from the waist down, and I felt it...the feeling of submission, of total need, total lust, the soft skin of a sissy. Something that no real man would ever do, but that I did.
So I dressed: black fishnet stockings, 5 inch clear heels, black thong, the pink jeweled plug - oh the plug - a black mesh stretchy minidress, long blonde wig and collar, and I was in. How could I ever get back now?
I made the accounts. Then he contacted me. He's a little bit older, and has many more years of experience in the life, and he understands the sissy mind better than I do, it seems. After a lot of chatting, and one phone call, I agreed to meet, finally.
He was getting "neutral ground" as he called it, a suite at a modern hotel for the weekend, even though I was planning on staying for a few hours at most. He told me to bring my favorite clothes for him, for the first time. I could have as much time as I needed to get ready. So I did, he had left a keycard for me at the front desk. I arrived in boyclothes with a rolling little carryon like any other businessman, got the key card from the desk, and went up the elevator.
Inside were two rooms, a large bedroom with a view of the city, and a living room with a big couch, desk and the usual hotel items, and there was a note on the desk. I read it.
"Trisha, get yourself ready as we discussed, then call me and I'll come up to meet you. -Daddy."
Oh wow, was he in the lobby watching me? I couldn't think about it; my heart started racing and I looked around. There's the bathroom, the bed, the closet. What to do first?
I tossed my suitcase on the bed and opened it. Inside was my dream life. The three outfits I had brought, all variations of the slut I had been becoming. I had already decided on black this time, as it seemed less vulnerable that the pink outfit I brought, or the slutty clubgirl outfit. I pulled out the items: first the 5-inch heel clear stripper heels with the ankle strap that gave me goosebumps every time I tightened the clasp, the brand new black thigh-high fishnets and their matching garter belt, the black lacy bra, the black thong, the black mesh opaque long-sleeve minidress, the black mesh short gloves, the black vinyl collar, the brunette wig, my new makeup bag, the pink jeweled metal plug, and the new metal chastity cage which has just arrived and I hadn't even tried it on yet.
I stripped off my boy clothes like a man on fire and started mumbling to myself, "Oh my god, i'm really going to do this? i'm doing this. i'm doing this. i don't have to do it again if i don't want to, i have to i have to."
I stared down at the bed, covered in clothes that only a whore would wear, or maybe a girlfriend wanting to do something special for her man one night, or a sissy like me.
Before I had arrived, I shaved all of my hair off below the neck, except my arms which I couldn't for work purposes, but I had a long- sleeve dress, and opera gloves for the other outfits. I had also given myself a thorough cleaning inside, not eating much for two days and i could feel my emptiness inside, both mental and physical.
I started to dress, piece after piece, my breath getting heavier with each one, getting hornier and more nervous, I can't believe I'm doing this, why why why me, why can't I be a real man, shut up and do it, it's so hot, you are a whore that's why, no no no, yes yes yes...back and forth until all the clothes were on except my wig, makeup, plug and chastity cage.
I stood up and walked on my heels to the full length mirror by the front door...oh my god, I'm really doing it. But I wasn't there yet.
"Put your plug in, whore," I heard a voice in my head say, and my clit twitched. I turned and went back to the bed, grabbing the plug and the cage, and a bottle of thick lube from the front zippered pocket. I strutted to the bathroom and pulled my thong down to my knees and bent forward. I pushed the top of the lube bottle down and dribbled a few drops onto the shining metal plug, then looked at myself in the mirror.
"I'm a whore," I said to myself, something I've said many times when fantasizing about this, but never like this, and I reached back and pushed the plug in. The cold steel against my little hole, then the stretch, then stretching more, then the pop in, and it sitting there so perfectly.
I looked down at my little cock, half hard from excitement and half soft from nervousness, and I opened the felt bag holding the metal cage and key and I opened the cage, fitting the ring around my balls. It was too big. I shook the bag, and more rings fell out. I took the smaller one, and fit it into the device, and tried it. Oh wow, it's tight, but I like it, i need it.
"Lock up, slut," I heard the voice in my head say, and I did. Pushing my - well, it's a clitty now - my clitty into the metal cage and locking it. It felt so good, so submissive, I can't believe it. It's not too late to run away, I thought. I can be out of this room in two minutes. I looked at myself in the mirror and smiled a little bit. I have to do it, i'm here, I need it.
I pulled up my thong, settling it between my cheeks, over my garters, and strutted back to the bed, grabbing the makeup case, and brunette wig. I took the desk chair into the bathroom and settled down on it. Oh wow, the plug and cage, I can feel them controlling me, as i opened the makeup bag and did a quick job. Just what I learned on my own. Eyeliner, a little eyeshade and a little blush, and bright red lipstick. That's all I've got so far. I look ridiculous, I thought. Look at me! A man, a straight man! Wearing makeup and dressed like this!
"I'm a hot bitch," I thought, and chuckled. Where did that come from?
Who knows, I need to hurry now I'm starting to freak out a little bit...I shook out the wig, and put it on, clasping it to my hair with some bobby pins. And then I stood up and walked back to the full length mirror.
"Yes," I said out loud to myself, "yes, I will."
I walked to the bed and picked up my cell phone, and dialed him. Daddy. That's the only name I know for him. He answered on the second ring.
"Are you ready, Trisha?"
"Good. Place the desk chair in the middle of the living room, facing the door, and kneel in front of it, with your back to the door. Do you understand?"
"Good girl. I'll be right up."
I quickly went to the bathroom and pulled out the desk chair, noticing my makeup items still everywhere, but it didn't matter. My stomach felt queasy, butterflies, anticipation. I brought the chair to the middle of the room, facing the door, and with one hand on the desk, I struggled to get onto my knees with my heels on, but I did. I kept my hands in front of me on my knees, should they be behind me, I don't know! I don't know! I was breathing quickly, nervously, looked up at the empty chair and I heard his keycard sliding into the unit, and the lock opening.
I heard the door open, and footsteps, and then the door closed. Silence. Then he stepped in front of me, black pants and black dress shoes are all I saw. He sat down.
-to be continued