This is a story about a first time crossdresser and some thrilling and occasionally demeaning sex. If you're into that kind of thing, enjoy! If you're not, or if you're under 18, or if this is illegal where you are, go play Minecraft.
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In the last chapter (from a long-ass time ago), I had just given a long and luxurious blowjob to Brendan, the man who seduced? raped? me on Halloween, a week earlier. We pick up with me on my knees and the taste of a load of cum in my mouth.
"Go fix your makeup. And get me a drink. And put on some music. And let me see you in your bra and panties. Because as soon as I'm ready, I'm going to fuck you."
I got up and went to take care of his needs.
"Be ready. Because when I fuck after I've already gotten off, I fuck long and hard."
I didn't doubt him.
Brendan was in the shower.
I took my handbag to the hallway bathroom. My makeup was not in too terrible of shape... I still looked pretty. Only my mouth was a mess. I put down another layer of lipstick and covered it with a thick layer of lipgloss.
I poured Jared a scotch on the rocks and took it to his bedroom. What a gorgeous space: simple decor, clean white sheets on the bed, floor-to-ceiling windows over the city. A masculine ideal.
Brendan's computer was open, so I put on some Sade in Spotify. Sade is what I would play when I wanted to score with a girl. The only difference this time is that I was the girl.
I reached behind, unzipped, and slipped out of my short black cocktail dress to reveal the black strapless bra and boyshort panties covering my smooth, white flesh. I folded the dress neatly and draped it over the back of his Herman Miller chair. I decided to leave my heels on--I thought that might look sexy.
I involuntarily grooved to the music, my hips keeping the beat and my body swaying to follow. I took in my own body, slid my hands down my smooth thighs and saw the girl in front of me in black heels, panties, and bra--a sexy girl getting herself ready for her man.
"Goddamn you're sexy."
Brendan came into the room with just a white towel on his waist. He sat on the edge of the bed.
"Move that ass for me."
I felt a little bashful, but I was under his command. I moved directly in front of him, swaying my hips and ass in rhythm with the music while touching my body. I tossed my hair, slid my hands over the edges of my panties. It came naturally.
"Turn around. Show me that ass."
I turned around to show him my petite ass. I bent over halfway, arching my back and presenting my ass a few feet in front of his face.
"Don't be shy, sweetie." I felt his big hands on the sides of my hips. He pulled me and I stumbled closer to him. Once I got there, he buried his nose in my ass and massaged my round cheeks with his strong hands.
"I was a little abrupt--a little rough--with this pussy last weekend. But today I'm going to take my time. Hope that's alright with you."
"Mmmmmmmm...." was all I could say.
"Lie down on your back, beautiful, and put your ass on the edge of the bed."
I got into position as instructed. I spread my legs. He gently but firmly tugged my panties off. I still had my heels strapped to my feet. I reached for them. He grabbed my wrist.
"Leave them on."
His fingertips began to explore my ass, the undersides of my thighs, the space between my balls and my ass.
"Your body--it's so smooth. Like it's ready for fucking."
I lay naked on the bed, tight stomach facing up, pussy in the air, heels on my feet, toenails painted, full makeup on my face. My dick was rock hard and leaking pre-cum like it had been since I started blowing him a half an hour ago.
Damn right I was ready for fucking.
Brendan, however, was not.
"Do you know what drives girls crazy? What makes them beg to get fucked? Getting eaten out."
His middle finger was on my pussy. He squirted a small amount of velvety lube on it and slid in just the tip. I moaned gently.
I had not expected him to service me--that was about the last thing I had imagined. But I was literally in his hands.
He wiggled his finger a little deeper into me, then added his tongue to the rim of my hole. It felt... strangely good, better than I expected. My dick was wicked hard in front and would probably have shot if a strong breeze had blown. But this sensation of pleasure was different. Deeper.
He fingered me a bit deeper, sliding his finger in two knuckles' deep, pressing up and inside me, hunting for my pleasure button.
He found it. I moaned as he pressed his finger over it.
He pulled his finger out, squirted more lube on them, then plugged two fingers inside me. I felt impossibly full but knew this was just the beginning.
My mind drifted to the time I finger banged Tara Zelinsky's pussy. My high school girlfriend, Tara had taught me about sex--how to finger a girl, how to eat her out, how to fuck her. Now, I was learning the same lessons--in reverse.
Brendan pushed my ass back so my legs were high in the air. I grabbed my heels to give him better access. He alternated deep diving with his tongue and working the wall of my pussy with two fingers. His tongue was driving me wild--like it was creating an itch that I could not scratch.
He added more lube and slid three fingers inside me. I moaned deep and long.
"You like that?"
I could only groan in response. His expert technique was taking me somewhere I'd never been. My pussy was aching yet begging for more. My thoughts were clouded by pure lust.
He went deeper, thrusting those three fingers into my warm and ready pussy. I was vaguely aware that he was studying my face, watching for signs of the pleasure he was giving, observing with delight the transformation he had created in me.
He lubed his hand again. Now he worked four fingers inside me. The threshold of pain and pleasure increased. My vision clouded over as he finger-fucked me. He went deep and played with my g-spot at the same time, playing my pussy like a master violinist plays a Mozart concerto.
"How does that feel, baby?"
"Ah--ah--ahmazing!"
"What do you want?"
"I want you to fuck me!"
"Beg me."
"Please! I need your big dick inside of me. I have to feel your whole big, thick cock up inside my pussy."
As he worked my pussy with his left hand, he reached up with his right and did something unexpected: he grasped my dick.
I shuddered in pleasure. He stroked it one, two, three long, slow times. I shot my cum explosively, my ass squeezing madly on his fingers. I cried out in deep pleasure, so loud that the neighbors on every side could hear me.
I had never had such an intense orgasm, yet, weirdly, it also felt incomplete--like there was another level still to be explored.
My eyes were opening to the possibilities of sex as a woman. Quite literally, as my vision began to return. Brendan was sweetly toweling me off with a damp, warm towel. My pussy was still dripping with lube.
But that was all part of Brendan's plan.
I came to, finally. My pleasure sensors had been over-stimulated and now went into much-needed rest. I saw the world with perfect, post-orgasmic clarity.
Here I am.
I was a man. I had dressed myself in women's clothing in an effort to appeal to another man--fuck, I'd even dieted and exercised to make him fuck me. I had sucked his cock and let him cum in my mouth. Now I'd let him eat me out and cum from just three strokes on my cock and the fantasy that I had a "pussy."
I looked up with the weight of this reality on my face, and saw Brendan above me wearing his arrogant smirk. As I opened my mouth to say something, to make an excuse, to get out of this situation in some way, in any way, he shoved his eight-inch dick up inside my ass.
I cried out in pain and shame. In this moment, the fantasy was gone. Brendan was simply and purely exerting dominance over me. What's worse is that I had begged for it, begged for his "big, thick cock" to fuck my "pussy."
As he slid all the way inside me, his thatch of pubic hair pressing against my shaven butt, my eyes welled with tears. He looked like he was in a state of true happiness.
He was getting off on my shame.
Impossibly full of dick and now stone sober, I looked up into his eyes as tears formed in mine. I opened my mouth but had nothing to say.
Brendan spoke instead.
"Do you feel me up inside you? Give me a squeeze in there. Make your master's cock feel good."
Embarrassed, I squeezed inside me, gripping my pussy tight around his dick.
"Ohhhh yeah. This is the fun part. And believe me, you're going to love it. You might not love it now, but that's part of the fun too. When we're done, you're going to wish you had my dick in you all day long, every day of the year."
I could already feel myself turning slightly lustful again, strangely glad to feel his pubes on my tight, smooth pussy lips.
What if he's right? What if I become a slave to his cock? I thought.
And that's when he started to fuck me.
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Did you like this story? I've got a couple of follow-up chapters in mind. If you'd like to read them, email me at sexyamie@hotmail.com