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 Angry Birds.
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When we last heard from our hero (me), I was dressed as a slutty schoolgirl on Halloween night, and was getting fucked in the ass by a stranger against my will. The last thing he said to me was, "meet me at the same spot next week."
After I wobbled my way home in the cold, getting sidelong glances from the couple of people I passed, I collapsed into my bed in my outfit. I could feel the squish of cum inside my ass and the wet spot in my panties where I'd come just from the feel of him fucking me so deeply. I reached into my panties and rubbed my dick, not like I normally would, but rubbed the front of it with two fingers under the panties like a girl. I touched my chest and my hard nipples with my other hand. Smelling his sweat and man-smell on my skin, I came powerfully in my panties, then drifted off to sleep, a happy, well-fucked girl.
The entire next week I couldn't get the incident out of my head. I was transfixed by it...and transformed by it. Up until the moment he penetrated me, I had been a completely straight guy in my mind. And for a second, the pain of having someone inside me was so great that I wanted to die. But then something clicked. His dick had fit so well inside me, and I couldn't stop thinking about it.
But what did he mean, "meet me at the same spot next week"? Did he mean the bar? The sidewalk? And surely he didn't mean that I should show up dressed as a girl again...or did he? It wouldn't be Halloween next week, so I didn't have a reason to go out like a girl. I must have looked like a total daydreamer at work, because I couldn't think of anything but what happened, and what was going to happen this week. My friends called me every day that week, probably wondering what happened to me when I left the bar that night (if only they knew!), but I sent all of their calls to voicemail and didn't return a single one.
I was fascinated by my own transformation, how spontaneous it was and how strong. No part of me even entertained the possibility of NOT meeting up with him. He was so commanding, and I was so happy to be dominated. I would meet up with him and I would...let him fuck me again? Jesus, I couldn't even think about it. But of course that was going to be what would happen.
As the week went on and I started to formulate a plan, my primary thought was that I didn't want to disappoint him. Obviously he wasn't interested in me as a man, so I couldn't just show up as myself. I had to dress again. But without the cover of Halloween, I'd have to put in some real effort at passing.
For starters, I needed an outfit. I settled on Forever 21--they had cute, young-looking and sexy clothes there. Plus, the prices were good, so I could get a few different things and mix and match. God, I WAS turning into a girl. My favorite was a short black cotton dress with mesh sleeves and shoulders. It was sexy but classy, like what the hot girl would wear to her graduation party. It was form fitting through the mid-section. Just to make sure I would look great in it, I started a diet. No starch, just protein and veggies. And no salt. I had to look slender.
I bought a real wig, not a cheap Halloween one. It was brunette, below the shoulder with some body to it. Very pretty. Forever 21 also had some costume jewelry to add to the look. And I picked up a week's worth of panties to wear. My favorites were the low-rise "boy briefs." The name was definitely ironic, because I looked like nothing but a girl in those tiny slips of fabric.
I knew I'd have to get my nails and makeup done, but since I didn't want to be revealed at work, I had to wait until the end of the workday on Friday. 5:00 couldn't come fast enough. I raced home, and started by shaving my whole body smooth. I don't know if you've ever tried to shave around your asshole, but it ain't easy. With practice (and I would get some practice) it gets easier, though.
I got dressed up in some of the more casual items I'd picked up: some black "hot pant" shorts that showed off my hottest assets, my legs and butt. Over that I threw a loose sweater that fell off one shoulder. I put on my wig and a little foundation. I stared at myself in the bathroom mirror--it was stunning how passable I was.
I walked to a manicure place in my neighborhood. The little Thai ladies treated me like I was any other customer, though they probably have seen it all, so I took their approval with a grain of salt. I got a French manicure and pedicure, then on a lark got my eyebrows waxed and plucked into finer, more feminine arches. I let the ladies do my makeup too: some smoky eyeshadow and a deep pink lipstick with a heavy layer of gloss. The women sold me extra lip stuff, knowing that I'd probably have to reapply it that night. How did everyone seem to know what was going to happen but me?
I was ready for a night out as a girl. Or was I? Jesus, I'd really taken this thing and run with it. Now I was going to put on a little cocktail dress and go be a flirtatious cockslut for the man who had violated me last week. What. The. Fuck.
I slipped into my dress and tried to let the second-thoughts slip from my mind. I pulled it over the strapless bra and boyshort panties I chose, black to match my dress. The dress looked incredible over my smooth, creamy thighs. I looked like the girls I used to lust after. I sat down, being careful to keep the high hem of my dress in a ladylike position. There I strapped on my new wedges, black leather with a four-inch heel. I could wear such tall heels and still be shorter than my date.
I didn't even know his name.
I had first seen him at the bar around 9pm, so I aimed to arrive then. I took a cab to avoid being seen and detected by my neighbors. The cabbie told me what a pretty girl I was and how lucky my boyfriend was tonight. I suppose he was right.
I clicked my way down the few stone stairs into the darkened bar. It was early still and the bar was pretty quiet. Shit, the same guy from last week was tending bar. I wondered if he would recognize me. I ordered a vodka martini, slightly dirty. The bartender complied and treated me just the way I'd expect him to treat a pretty girl, though he did seem to do a bit of a double-take, like he'd just had d‚j… vu or something.
I sat on a stool and put one thigh over the other one, coyly. I loved the way that the slender martini glass looked in my manicured and extended nails, and the sound they made as they clicked against the glass. Before I knew it, the glass was empty. Jesus, I must be nervous, I thought. I put the glass on the bar and ordered another.
What makes a man put himself in such a vulnerable position? Here I am, wearing heels, makeup, jewelry, and a sexy little dress, drinking too much and waiting on a man I didn't even know. He had captivated me; he had owned me, and now I was back for more.
I was halfway through my second martini when I saw him. My heart thumped--after all this waiting and prep, I had barely thought about what would happen when we actually came face to face. He glanced around the room confidently, spotted me and walked over, staring at me with a smile that was half-sweet, half-smirk.
"I'm so glad you came." He put his big hand on the small of my back and kissed me on my foundation-covered cheek. "You look fucking hot."
It was a compliment but had a primitive tone to it, like, you look hot, and I'm going to fuck you. "Thanks."
"I didn't get your name last week. I'm Brendan."
"Hi Brendan, I'm...Amie." I gave him my hand in a little feminine half-handshake. I've been a woman for all of 4 hours of my life and I've already got the mannerisms down. How did that happen? Somehow he put my in place...it came naturally with him.
He moved in so that the leg of his khakis was pressed lightly against my shaven left leg. We talked closely, like two people who are extremely hot for each other. And, uh, that's what we were. "What are you drinking?"
"Martini."
"Bartender, another round for the lady and a scotch for me." The bartender walked over and started to make our drinks, then looked up like he just remembered something. He looked at me, looked at Brendan, and put it together. He gave me a raise of the eyebrows and a shake of the head. I'm sure he's seen just about everything, but a Halloween slut who comes back for seconds...well, that might have been a first.
We nursed our drinks. I have a high tolerance but I was getting plastered. I'd been dieting all week so that I'd look amazing in this slim dress, and the lack of body weight meant that the booze was going straight to my brain. I had to stop myself mid-drink. I turned to Brendan and said, "take me home."
He smile/smirked again and said, "let's go." He grabbed my hand, which I interlaced in his. He helped support me on the way out. As we walked out of the bar, not 3 blocks from where he raped my ass last week, we looked like sweethearts, a hot young couple with everything going for them. No one could tell that I was a degenerate slut with a brand-new craving for hard cock.
He took a turn that went away from my place. I didn't know where we were going. A hotel? His place? Or was he just going to find a dark corner and abuse me again? We stopped in front of an old brick building. He turned the key and let me in. His place was a massive loft, one colossal room with exposed ductwork. There was a bear-skin rug, some modern sofas, an open kitchen, and a king-sized bed all under 15 foot ceilings.
He had one thing on his mind--you can see it in his face. Jesus, men are predictable. When they want to get their dicks wet, that's the only thing in the world that is important. And this man wanted me to take care of him. He crashed onto his sofa, his arms spread wide and his legs open. His body took up nearly the whole sofa. His body language clearly told me: kneel.
Well, that was not what I thought would happen. I really didn't know what we would do, but...I had not imagined that I would blow him. That was so one-sided, so passive, so...feminine. I had made crossed a line rather quickly, but this was a barrier that I wasn't sure I could cross. But I didn't want to disappoint him. I walked drunkenly towards him with my hips swaying. I slowly dropped to my shaven knees, locking eyes with him the whole way. No conversation was necessary.
He unbuckled his belt, unzipped his pants and pulled his underwear down to reveal his semi-hard, gorgeous dick. His big, hairy balls drooped below. I was immediately hit with the scent of his groin. It was masculine: musky and slightly ripe, but somehow divine. His masculinity was so clearly superior to mine. His hairy balls reminded me that I had two little balls too, they were just shaven, perfumed, and wrapped up in panties under my dress.
He stroked his dick slowly, and pointed it in the direction of my face.
This was the point of no return. I could leave right now and only have been the unwilling victim of a sexual predator. I could leave here and forget that this had ever happened. Or I could humiliate and degrade myself by submitting willingly to this man, admit that I wanted to please him by making his cock explode in my mouth. The decision was entirely mine, and it would define me and my status as a man.
I leaned forward, grabbed the base of his cock with my little hand, and gave the head of his dick a French-kiss. He already had a drop of pre-cum on his slit, and I tasted it and rolled it around my mouth.
Decision made. I was a bitch. A slut for cock.
I wanted to give him the blowjob I always wanted but could never get from a girl. I felt like I knew how to please a man. I started by licking his dick from base to tip slowly, making eye contact the entire time. Then I slipped the whole head into my mouth and rotated my head around it. He moaned and leaned back deeper into the couch. I was off to a good start.
I alternated sucking on just the sensitive knob and allowing his dick into my mouth. Hard, he was a thick eight inches, bigger by far than my average 5 1/2 inches.
I took as much in as I could and started to build a slow rhythm. With just a little practice (I was a natural!) I got six of his eight inches into my mouth. I completely surrounded it with my tongue and mouth. I slurped his cock deep into my mouth, being careful to keep it off my teeth. I applied a little bit of suction as I continued to let his big dick slide in and out of my mouth.
I must have been doing a kick-ass job, because he was moving his pelvis around and moaning deeply. His eyes were rolling back into his head. I loved all the signals I got, and was inspired to make his dick feel even better.
I decided to go full deep-throat on him. I let the last two inches of his thick one punch into the back of my throat. I coughed and gagged a little bit. My eyes teared up. I was so embarrassed. I wanted to get his whole thing in my mouth and throat so bad. I tried again, coughed again, and had to let his dick slip out of my mouth while I recovered. I stroked him with my hand while I looked up at him apologetically.
"It's OK, baby. You'll get it over time."
Over time. I just needed practice. I'd be sucking his cock again. The thought was hitting me as to what I was doing here. I was a committed cocksucker. Not only that, but once I got him off in my mouth, I would want him to fuck my ass again. Of course, part of me knew that--that I'd submit to him in every way possible, get used by him in every position he could think of, but now it really hit me. I'm a cock slut, I'm this guy's cock slut, I'm going to dress for him and blow him and take his cock up my ass as often as he wants.
So here I was on my knees in my cute little cocktail dress, kneeling in front of this clean-cut 6'1" stud with his 8 inches of masculinity. My tiny dick is so rock hard it's about to rip a hole through the skimpy panties I'm wearing. His pre-cum is covering the inside of my mouth, and I'm picking up the rhythm of having a thick eight-incher pumping in and out of my mouth.
My knees and jaw were starting to get sore, but it wasn't about me. It was about giving Brendan the most explosive, pleasurable experience he could have. I increased my suction. I picked up my pace. I met the rhythm of his hips pulsing slightly upwards. He was getting closer. I felt him get even harder in my mouth, the veins on his dick pulsating along my tongue as I sucked him. This was the best blowjob I'd ever had, and I was giving it.
Brendan starting moaning deeply. I could tell from his sounds that he was really close. I kept right at my pace. I would get him off using my pussy mouth alone. I felt his dick begin to pulse.
He cried out, "OH GOD!" He arched his back, sticking his dick deep into my throat.
His dick throbbed and jetted a load of hot cum into the back of my mouth. I kept up my pace as he shot another load, equally large. I kept it going for him as my mouth was filling up. He pulsed his jizz into my mouth a third, fourth, and a fifth time. Some hot salty-sweet cum dribbled out of my lipstick-covered mouth. I slowed my pace as he softened. His arched back began to relax. He crashed into the couch, his face screwed up from the intense pleasure he had just felt. We had communed over his dick, over a finely-tuned, perfectly-connected blowjob in which I told him, "I am yours. I will give you pleasure because you are what a man should be." And hardly a word was spoken.
I fell back onto my heels. I swallowed the large load of cum he'd shot in my mouth and used a polished fingernail to scoop what was on my face into my mouth as well. I wanted it all.
For 30 seconds, I watched his face in feminine pride. When he finally came to again, he said, "That was incredible. You're the best cocksucker I've ever known."
"Thank you," I said demurely. Thanks for letting me have that beautiful dick.
"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.
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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