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 Fortnite.
+++++++++++++
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.
I could taste his cock in my mouth still, the cock that had shot a huge load into my mouth and down my throat.
Now that cock, fully engorged again, was inside me.
His warning--"When I fuck after I've already gotten off, I fuck long and hard"--echoed in my head.
He started to piston his limb inside me. Both of us post-orgasmic, we could see with utter clarity, feel what was happening with perfect lucidity. We locked eyes, both aware of the moment, united by his thick cock sliding in and out as my tight pussy clinged onto it, milked it, felt it, made love to it.
He smiled again, this time without the malice and arrogance--now just with the joy of sexual victory, of knowing that something great was about to happen. He looked like a kid the night before Christmas. The only difference was that he was not excited that Santa Claus was coming to town... he was excited that he was going to come up my ass.
It would take awhile. We would connect over that dick, feel it moving inside me in every way possible, for over an hour and a half. I would discover (then rediscover, then rediscover again) anal orgasm. He would fuck me on my back, on my knees, clinging to his shoulders, pressed against the wall, standing on my tiptoes, and finally with my feet on his shoulders--every way it feels good to put a monster penis inside a tight hole.
For now, though, I spread my legs while he fucked me the traditional way.
I could start to appreciate my position. His manliness--the way he handled me, his thick muscularity, his slightly-rank man smell--created in me a sense of longing. I wanted to be as close to this man as I could--to give to him all of myself that I could. I ran my hands over his chest, feeling his thick pecs, my fingertips running through the light patch of chocolate-colored hair above them.
He would get hairier there as he got older, I thought. Become more of a man. I dreamt of being under him then, too, my body still shaven smooth, taking a firm fuck from a middle-aged man's cock.
There was no need to fantasize, though--I was getting worked over by a young man in peak physical condition, his Greek God stage. I looked up and saw just a glint of sweat on his forehead, his tousled hair perfectly messy, the hint of scotch on his breath as he exercised within me.
I looked at myself. Was I fit for the challenge of mating with this divine creature, this Hercules? My French manicured toenails peaked out the front of my patent black kitten heels. The light silver anklet I wore slid over my pale, thin calf. My lusciously smooth skin from my toes up through my thighs, even up to my... my pussy. My flat stomach, just like on the hottest girls, the ones I used to dream about, then dreamt about being. Now I didn't have to dream--I was one of them.
I was a hot girl. A 10 out of 10 (plus a cock).
Brendan took each of my skinny wrists in his hands and held them on the mattress above my head. He kissed inside my smooth armpits, kept fucking me. I tightened my core muscles, pulled my legs up-and-back to give him greater access. His chest was just above mine and rubbed against it. He slow-fucked me steadily, insistently. His face passed by mine as he thrust in and out. Our noses touched once, twice.
We had never even kissed, I thought. I'd taken two massive loads from this guy--one in each end--and I'd never had so much as a peck. If he was going to kiss me, it didn't happen then. So I watched his face as it slid just in front of mine, saw the expression of a man who was just starting to enter the stages of arousal.
Our bodies were starting to sweat. I could feel the light glide of his skin against mine, the sheen of moisture a conductor for the electricity between us. I reached for the heels of my shoes, pulled them further back to get more dick inside me. His chest rubbed harder against mine, brushed against the bra I was still wearing.
"Take your bra off."
I reached behind my back to unhook my bra, engaged my legs to keep them up and not interrupt the fuck.
I slid the bra off my arms. Our naked chests rubbed together. Did I look less feminine, less like a woman without my bra on? Brendan must have read my mind.
"You look beautiful, baby. So truly fuckable."
I blushed, committed myself again to giving him the best fuck I could.
We began to leave the civilized phase and enter the lustful one. I could feel the rib of the head of his dick sliding deeper in me. He was pounding my bitchass deep and hard.
I squeezed him off, newly aware of the musculature inside of me.
Brendan moaned. I massaged his member as it rode over my inner sphincter. Bent at the midriff like I was, it felt like the head was pressing into my stomach: he was that big, took me that deep.
We both started panting as he fucked me a little faster. He was trying to get me pregnant now, shoot a load high and deep inside my willing pussy.
But his goal was not to cum. At least not soon. His thick dick was firm but not impatient, and he ran his dick up in me steadily.
He pulled near my entrance and did something a little differentÑhe lifted my ass up above me so his dick could drive harder against the front of my pussy wall. Then he sunk his dick inside me, just 3-4 inches up inside my pussy. He pressed up on the spot where his fat dickhead landed. I could feel something inside me, a sensation building slowly. I didn't know it then, but he was pounding on my g-spot, my pleasure point, pounding the head and ridge of his dick right on top of the spot that could drive me crazy, could set me free.
He hit it over and over again, my hands again pinned up behind my head, sweat beginning to drip from his chest onto mine. Our foreheads touched, connected as kept hitting my spot. He looked into my eyes, desperate to see the effect he was having on me. I squealed.
I started to lose my full vision. I saw stars on top of the world as the pressure of his thickness, the pain and pleasure of it increased in my body. I started making sounds, noises that you can't describe, animal noises that belong to a deeply rutted wild animal. I could no longer contain myself as he landed on my pleasure spotÑit was almost too much, but somehow never enough.
He rubbed my breasts, which sent another wave of pleasure through my body. Waves upon waves of pleasure built on each other, added together. My legs spasmed. My throat caught my breath as my body expanded and contracted.
I was having a full-on pussygasm.
Brendan saw this but just kept hitting my spot. I moaned, cried out, clawed at his chest as he brought me to this level of pleasure. I was powerless, but electric. I was fulfilled completely and yet totally unfulfilled.
If you've ever had an orgasm from your ass, you know what I am talking about.
If you haven't, it's like being on the verge of cumming, constantly. Never that full release, but right up at the edge, getting pulverized, hammered by the pleasure.
I lost my mind with pleasure I forgot my name, forgot how to speak for fifteen minutes. I went into a world of pain-pleasure that only ended when Brendan slowed down to look in my eyes again.
"How was that?" he asked.
I welled up with tears. "Incredible. I don't... thank you."
He started fucking me deep again as the smile returned to his face. He was still so far from cumming, so much the master of his hard cock, that he could just talk to me: man-to-pussybitch.
"I always want to see my bitches cum while I fuck them. I know I'm going to cum, so that's not the fun part."
As he's chatting, meanwhile, he's insistently fucking his eight-incher inside of me.
"But seeing my bitches get off from having me inside them? Well, that's almost as good as when I come. Almost."
"Now, I want you to fuck yourself."
He grabbed me by the hips. He lifted me off the mattress, pulled me onto his lap. My clitty was pressed against his hairy chest as we got resettled. That didn't seem to bother him a bit.
I climbed on top of him as he lay down. I put my hands on his chest, feeling the pulsing of his heart through his wall of chest muscles. I ran my hands down to his abs, traced the pattern of his six-pack. He was such a fucking stud.
"I said fuck yourself."
I snapped out of my reverie at his command. I placed my knees wide to the side and braced myself with my hands on his strong chest. I worked my hips up then down again, releasing three inches of his length then sinking back down onto it entirely.
Mmmmmm, that felt good.
I decided to go deeper.
I rolled my body up, tucked my knees in, and arched my back high so that he was only in me an inch or two... then lowered back down on him all the way.
We both sighed. I did that move again, letting the fullness of him run through my tight passageway.
It was so hot I could barely do it a third timeÑI might cum through my own dick from how good it felt.
"Get selfish, baby. Make that pussy feel good. I'm gonna get mine; don't worry. I wanna see you wiggle on it."
He was lying on his back, pulled a pillow up under his head, got relaxed. I had his dick nestled inside me. I leaned forward and placed my knees further up his sides. Now his dick was just barely inside my hole. I placed my hands on his chest and began to work the tip inside me. I found my pleasure spot and whimpered. I took a quick breath then bounced on that spot once, twice, three times. It felt so good that I couldn't stop. I worked the head on my spot over and over again, crying out "Unnnhhhhh! Unnnhhhhhh!" The pleasure was driving me wild. I was worried I would cum both from my ass and my dick at the same time.
He put his hands on my flat tits, pinching my nipples roughly as I worked my ass. He stuck one thumb on top of my lips. I took it into my mouth, began sucking it like it was his dick.
I fell into my whimpering second ass-orgasm, moaning and whining. It lasted and lasted as I worked his dickhead inside me at all the key pressure points.
I was living for this big dick inside me.
After I came (up the ass), I breathlessly let myself rest on Brendan's chest, his dick engaged inside me. Brendan took the lead again. He slapped my firm cheek and told me to get off his dick entirely.
"Get on your knees and spread your legs like a bitch."
I could barely understand his words but I could hear his intention. He was going to fuck me hard. I flipped myself over, put my knees wide to the side of me and arched my back downwardÑthe sluttiest position a man or woman (or I) could take.
My ass hung over the edge of the bed.
He sprung to the floor. With his 6'1" height plus the height of the bed, I had to wiggle my ass downward, spreading my knees and opening up my ass wide to give him open access.
Once I was there, he leaned over me, his hand around my midsection.
"Do you remember this position? On Halloween? This is how we started dating, sweetie."
He jammed his full cock up inside me, hard and fast. Did he just make a sarcastic reference to when he raped me?
"Just like that. Mmm. Still a perfect fit for my big one."
I made a noise of approval.
(It's pretty hot to know that he's right, that my pussy is built perfectly for his dick. It's 100% emasculating, but to be a good fit for this man, fuck... I'll be a woman any day.)
He rammed inside me, pulled nearly all the way out, then rammed in again, hard and fast. I gasped as his hairy crotch pressed against my sweet, bare ass.
He did it again, sliding seven of his thick eight inches into me with energy and force.
He'd let me have my pleasure; now it was his turn.
He moaned from the tightness. I gasped from the shock. It was the Brendan Show now. It would be until he let his cock blow off inside my ass, or wherever else he wanted to shoot.
He thrust inside me at various angles, hammering the sides of my still-new pussy-ass. He changed the angle as he thrust in, widening my pussy with every landed blow.
"I'm gonna wreck this pussy."
That sounded like a threat.
Giving him my pussy this way was like passing the key to your brand new Tesla to your testosterone-laden 17-year-old son and telling him to have fun. You hope you're getting the car back, but you KNOW it's coming back with some wear-and-tear.
Sure enough, he was driving me fast and furious. He pounded into me again and again. His shouts were louder than before. If the neighboring apartments had heard me while he was eating me out, the whole building could hear him while he fucked me from behind.
I could only hold on, keep my ass low, opened wide, take his stallion dick inside me the best way I could. I met his thrusts, opened up inside, squeezed him at the top, and tried to make his horny-ass dick feel so good it would throw up its load of cum.
Not yet, it wouldn't. After 15 minutes of fucking me hard and deep, he grabbed my feet and flipped me over. With my feet on his shoulders, he grabbed around my neck and I supported myself on his. He picked me up and started fucking me in thin air, bouncing me off his dick with just the violent weight of gravity pulling me down onto his thick one.
Determined to push ever deeper into me, he moved from there to the wall. My sensitive back lay against a painted brick wall. He used the pressure of the wall to hammer deeply into me. Between the friction of the wall and my own weight pulling me downward, his dick was so deep inside me. Maybe the deepest it had ever been.
He looked into the full-length mirror that ran alongside us, that showed our full fuck position. I took in his muscular ass, saw where the front of his hips nested inside my pussy-ass. "Look at yourself. Didn't you used to be a man? Now, you're getting fucked like a slut. And you fucking love it."
I took in his demeaning words, realized I could not deny the truth. I was essentially a fuckslut--someone who got off on getting men off.
He bounced me up and down a couple times as we stared at ourselves. I yelped involuntarily.
I was a fucking slut, just a week and a day removed from being a straight man.
"I do love it. Now give me that dick, and give it to me hard and long."
Brendan pressed into me, making me feel the hard head of his dick in the pit of my stomach. He lifted me off his dick and instructed me to "turn around."
I had my hands against the bricks. He spread my legs with his, fumbled for my hole.
"Get up on your toes."
I had my heels on, but Brendan is six inches taller than I am. I pressed into my toes, my knees scraping up against the wall. He pressed into me from behind, popping nearly all the way into me once he landed on my hole.
I almost exploded out of pleasure.
"Oh yeah, bitch."
He reached in front and gave my dick a quick couple of strokes. I was rock hard. I gasped as he touched it.
"I knew you were going to love this."
He took to fucking me against the wall. I let my dick rub against the smooth brick surface as my body pressed into the painted brick. Even that hard surface was turning me on, as aroused as I was.
Brendan worked me out there. My face was pressed red once he let me off the wall. I struggled to find my legs, naked but for my kitten heels.
"I want to finish off in your sweet pussy. But first, show me again how good you suck."
I dropped to my knees and breathlessly took his thickness in my mouth, slurping it around my mouth like a porn star. On his dick I could taste lube, precum and my ass. It was a musky combination--a taste that I would grow to love.
I worked his dick hot and fast. "OK, I'm ready to fuck you. Get on your back and spread your legs."
I dropped to the bed and grabbed the backs of my heels.
Brendan landed on top of me and promptly sunk his dick inside me. We fit perfectly--we really did. I was designed and built to take this man's cock inside me, I thought.
He stared me in the eyes as he fucked me deep. "You're a fucking faggot--you know that, right?"
I nodded, smarting at the word `faggot' but knowing... truly, I was. I was his faggot, his bitch, and I would do anything he asked me to do for him.
He sank into me, our foreheads touching. His sweat dripped onto me. I moaned softly, so fucked-out that despite the ongoing stream of pleasure, I was exhausted. Completely fucked.
He rammed into me until his pace quickened. He was ready to shoot.
"I'm gonna cum inside you baby. Grab your dick and cum when I do."
I stroked my dick, so sensitive that I could barely touch it without cumming.
He took his pace up, began a crescendo of a moan, then with a gasp shot his fat load of cum as deep inside me as he could.
The sensation of a man getting off up my ass was too much; I shot my huge load all over my pretty, painted fingernails.
We both came for 45 seconds or so, moaning and crying out in ecstasy as we did.
It was the best fuck I'd ever hadÑgiving, or in this case, taking.
He collapsed on top of me, his softening dick still inside my hole. He took a nap on top of me for five minutes.
When he woke up, he pressed off of me, a little disgusted by what he saw in my face.
"You gotta go. I got some work to do."
I rolled to the side of the bed.
"Just close the door behind you, it locks."
He collapsed onto his bed. Was this the work he had to do?
I got up and wobbled my way to the bathroom. I was sore as fuck and trying to keep a huge load of cum inside me. What was I trying to do, get pregnant?
I got to the bathroom, saw my fucked-out face. I was certainly not as pretty now as I was when we started, that's for sure. But I'd given him a terrific fuck, at least.
Once I was dressed in my cocktail dress again and at-least-half-decent looking, I snuck into his bedroom. He was asleep and snoring. I left him alone.
After that night, I could not wait to take another fuck from him. I wanted his dick from the front, from the back, from the side. I wanted to suck him into ecstasy. I wanted to do for him whatever he wanted me to do for him.
I was obsessed with him.
Brendan, however, was not obsessed with me.
I didn't hear from him for a couple of days. On Tuesday I texted him a simple, "hey, what's up?" No response.
Wednesday came and went, then Thursday, then Friday...
I had been secretly hoping to spend the next weekend locked onto his dick.
"Any plans this weekend?" I asked.
No response.
I started texting him something sexual. Once per day. "I love your big beautiful cock." "I have to feel you inside me." "Fuck me hard." That sort of thing.
For another week-and-a-half, I heard nothing back from him. Till finally, out of nowhere, I got the following message.
"Hey sorry been busy. get your friends together I want to meet them."
What the fuck was that supposed to mean?
+++++++++++++
Did you like this story? I've got exactly two follow-up chapters in mind. If you'd like to read them, email me at sexyamie@hotmail.com