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I spent two-and-a-half weeks obsessing with Brendan.
I watched my diet to trim my figure even tighter than I had so far. I did squats and lunges every day to plump my ass. My slender midriff now sat inside my plump hips by a good two inches. I kept my eyebrows plucked, my face, legs, and armpits smooth-shaven, just in case Brendan wanted to see me right away.
And it wasn't just physical, either. Every thought I had was about how I could give him a better fuck, to make his big dick feel better in my mouth, in my... pussy... I had even started to call it that to get into the proper mindset.
I was physically and mentally ready take his dick inside me anytime or anywhere he would give it to me.
I texted him every day with something sexy.
"I want your thick fucking cock inside of me." "I want you to get my pussy ready and then fuck it as hard as you want." "I miss the taste of your dick."
But he never wrote back.
All the while, I was living and hating my straight life as Jeremy. I femmed it up a little at the lawfirm. I wore panties under my khakis.
I wore a bra--that was a small risk. Fuck it if they saw it.
I took it further. I added a subtle line of eyeliner and wore a dress shirt that was really a women's shirt. Guys wouldn't notice, but women's shirts button the opposite way. Plus, the cut is, well, a little more femme. Some of the guys in the firm did double takes--I think they might have been turned on. The young receptionist told me she thought I looked pretty.
Finally, after two weeks of waiting, I got that text message: "Hey sorry been busy. get your friends together I want to meet them."
What did that mean? He wants to meet my friends?? I guess he saw them when we were at the bar on Halloween... but what does he want with them?
I reached out to my bros--Pete, Joe, and Bryan--over a group text: "hey, long time no see! you guys free on Saturday?"
Pete was first to get back to me: "He lives! Where the fuck you been?"
Joe: "yeah, what the fuck, homo? havent seen you since you walked out on us on halloween."
"Just been busy. You free Saturday or what?"
I got a yes from my boys and texted Brendan to let him know.
"Great. Tell them 1:15. I'll be there at 12:45."
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I didn't know what Brendan expected from me. I also knew better than to hassle him with a thousand texts. I just sent one: "What should I wear?"
"Wear what you normally do."
Very helpful. I think that's when I began to realize that Brendan was kind of an asshole. Unfortunately, that did not make him any less attractive to me.
I decided to go fairly neutral for Saturday, wear something that could skew either femme or 21st century hipster: tight jeans cuffed at mid-calf, a loose fitting, light t-shirt with a plunging neckline, a pair of low-cut Converse All-Stars. I did light makeup--foundation, eyeliner, a little mascara--and styled my own hair, which was growing in longer now. I looked like a boy who was going out to a club on a Saturday night--a boy who might either take a girl or another boy home.
Underneath that, I shaved my legs and worn panties and a bra. I hoped that after my friends left that Brendan would have his way with me, and he certainly would want me en femme, ready to fuck.
Brendan arrived right on time. He brought one bottle of scotch and one of pinot grigio.
He looked me up and down, without judgment, without warmth. "Go and change. You look like a boy."
I was momentarily hurt, showed it in my face. He did not care or respond.
"Do your makeup too, with lipstick. Don't you want to look pretty for your friends?"
I retreated down the hallway. He called after me.
"Leave the hair, though. Your hair looks hot."
I scurried away to my closet. I was embarrassed and ashamed that I had not pleased Brendan but secretly excited to dress a little deeper.
What the fuck would my friends think?
I picked out a sundress in a flower print. The dress caressed my super-skinny midsection and went mid-thigh in length; the material was so light I practically had to hold it down to keep from being exposed. I wore knee-length calfskin boots with some fringe on them. I did my lips in a reddish-pink, plus a coat of gloss. I added light eyeshadow in a shimmery sky-blue.
I looked in the mirror. I looked like what I was: a super-femme, slightly-slutty crossdresser.
The buzzer rang.
My heart stopped.
A voice rang through the intercom: "It's us! We're here."
"Come on up," replied Brendan.
I froze. What was I supposed to do, go out there? Sit on Brendan's arm? I barely even know this guy... what was I supposed to do, introduce him to my friends?
The guys knocked on the door. Brendan let them in... the confident jackal.
"Come on in fellas. I've heard all about you guys. Can I get you guys a scotch? A white wine?"
I slammed my door shut. I looked in the mirror again: now I looked like a stressed-the-fuck-out crossdresser.
I could hear conversations out there, could hear Brendan making them laugh. Were they uncomfortable? Was he talking about me?
I had to step in. As I hit the doorway to the living room, I heard Brendan.
"There she is."
I stepped into the threshold.
Pete. Joe. Bryan. All staring at me. Dumbfounded.
Joe's jaw dropped, literally.
"Hi... fellas," I managed.
Bryan adjusted his pants.
"So you can see that Jeremy is now Amie. She's been fucking me since Halloween--since you last saw her, in fact."
"And man, she fucks like a champ."
The guys were dumbstruck. Pete finally piped up.
"Is it true, Jeremy?"
"Call me Amie," I replied.
I blushed.
"Are you--transitioning?"
"I don't know. I don't think so?"
"Amie... I think you're really, really, beautiful."
That was earnest, sweet Joe. I could tell that he meant it.
"I wanna fuck her in the ass."
That was Bryan... and we all could tell that he meant it too.
"Boys, what you do with her is up to you. She's a world-class cocksucker, and she fucks even better. So you really can't screw this up... unless you don't do anything at all."
The guys shifted around uncomfortably. Brendan had invited them to take advantage of me. They weren't really the sort to do that kind of thing, though.
We sat around for thirty awkward seconds. I took in the room. Pete had a scotch, could barely look at me. Joe had a white wine and was looking at me with pure admiration. Bryan--scotch--looked at me with eyes like he was the devil himself.
"Man, Amie, your friends are shy! Let's show `em what you can do."
Brendan gestured me to come over to him. I walked over, stood next to him.
He snapped, pointed at the ground. I looked at my friends. They were fascinated, on the edges of the sofa waiting to see where the fuck this was going.
I kneeled, climbed between his legs. I reached up, unbuckled Brendan's belt, and pulled his pants down.
"Fuck you," I said to him, genuinely hurt and humiliated.
"You're going to thank me for this."
His thick, hard cock--the one I've been dreaming about for the past three weeks--flopped out, semi-hard already. I took it straight into my mouth, no hands, slurped it all the way to the back of my mouth.
"Holy shit," said Pete.
"That's... that's hot," said Joe.
I worked his cock sensually until it was all-the-way hard. Brendan stood up so I was now in profile on my knees. The guys could see my technique all the way--could tell how good I was, how much I was enjoying it... which I was.
"So you can see... she's pretty great at this."
The guys were slightly less shocked now and maybe a little bit horny. I could feel Pete's gaze on the side of my face, right where Brendan's cock met my mouth.
"I've put a load in her mouth and several in her ass. I want you guys to get a shot. What about you? You look like you're horned up."
Brendan nodded at Pete. I glanced at him, cock still in my mouth. Yep, Pete definitely had a fucking boner.
"Come here, bro... this'll be hot."
Pete stood up like the devil was leading him. He stood next to Brendan.
"Amie, get your friend ready."
I looked up into Pete's face. He had a combination of nervousness and pure desire.
I had desire too...
I grabbed Pete's jeans at the waist, ripped them down without undoing his belt, and stared at the second cock I'd ever seen in front of my face in my life.
It was semi-hard and not as big as Brendan's. Had an upturned curve that started to show. Surrounded by a thick thatch of brown pubic hair. I moved my nose an inch from his crotch and took in Pete's smell. It smelled like he did, just a little more rank. Ripe. Manly.
I looked up into my friend's eyes. I moved my lips to the tip, pulled him into my mouth with my tongue. Slurped hard down the length of his cock.
It's amazing--you can feel a cock grow in your mouth on the first suck when you do it right.
He thickened up. I ran my mouth up and down his rod. Brendan put his arm over Pete's shoulders. "Isn't she fantastic?"
"Sweet Jesus..." was all Pete could manage. I wanted to work his dick beautifully, reward him for being the first brave soul to get a blowjob from me. Out of the corner of my eye, I could see that Bryan had whipped his cock out and started to jerk it feverishly.
Pete stretched to seven-plus inches, a little wider than tall, with an upcurve that caused his dick to rub against the roof of my mouth. I worked him hard, keeping eye contact as much as possible. I tried to give him a blowjob that felt like a wet, hot, passionate fuck.
"Oh Jesus, Jerem-- Amie. I'm not gonna last long if you keep going like that."
I kept going. I reached up with my right hand, held his balls, gently stroked his taint. That sent him over the edge. "I'm gonna cum..."
I kept working him the same way. I wanted him to cum hard and deep in my mouth.
And he did. His first warm shot leapt over the back of my tongue and into the back of my throat. I kept thrusting passionately. The next spurt hit the front of my mouth and coated my tongue. I kept working Pete as kept shooting, his knees buckling from the pleasure.
He kept thrusting, his eyes closed, a look of anguished pleasure on his face. I worked the last drops of cum out of his dick gently, cleaned off his dick, which had shrunk, totally spent from his huge orgasm.
Once he came to, Pete exhaled. "That was the best blowjob I've gotten in my life."
"I wanna fuck her now!" yelled Bryan.
"Patience. You've got to warm a pussy up before you fuck it." Brendan was such a strangely calm advisor to these guys. He was controlling the room just as he had with me.
"What about you, bud? You look like you could use a hot blowjob." He looked at Joe, who looked like he was surprised to be called on. Joe, always, the kindest of my friends, would be the last person to take advantage of me.
Still, he was horny. Hypnotically, he stood up and walked to the other side of Brendan. "Amie, tell him how much you want to suck his cock."
"I want to suck your cock so bad, Joe. I want to make you feel so good."
Joe exhaled choppily, swallowed hard. I reached up, delicately unslid his canvas belt, pulled his cargo shorts and briefs down.
His thighs were muscular and a little hairy. His dick was already dribbling precum. It poked up straight, about six inches long. I thought to myself, oh yeah. I can make this dick feel amazing.
I gave him a long lick over the underside, from the base up to the tip. I licked his precum. "You taste amazing, Joe."
"Unnhhh...... thanks..."
I teased the head for a little while, rolling my tongue in circles around it, popping the head and an inch of the shaft in my mouth. I squeezed that part with a firm suction, gave him a good quick sucking.
I looked up to check my work. Joe was mesmerized.
So too was Brendan, who was stroking his dick. Joe noticed too, saw that Brendan sported a full two more inches than he did, plus added girth.
"You ever seen one that big?" asked Brendan. Joe shook his head. "Here. Hold it."
Brendan took Joe's left hand and wrapped it around his own dick. "Now, stroke it for me."
I could feel Joe's dick, already hard, swelling to max capacity as he felt Brendan's big dick. I felt a little jealous that he got to touch Brendan, my Brendan, but I did not want that jealousy to affect my work. I laid my two hands on Joe's thick, hairy thighs, worked to get him off with just my mouth.
Brendan had begun to leak precum too. "Taste it," he instructed Joe, who tentatively stuck the side of his fingers to his lips. "Not bad, huh?" Joe shook his head. His dick swelled again... he had to be close to popping off.
"If you want I'll give you a chance to suck it." I stared up to see Joe's reaction as Brendan baited him. He had a nonverbal response--he immediately started shooting his cum into my mouth. I caught the full load: it tasted mostly sweet, with a nutty muskiness that I adored.
Brendan winked at Joe, his arm around him as he came down from his orgasm.
"My turn," announced Bryan. This fucker... what was his deal tonight? He was putting us all on edge.
"Let her lube herself up first. Amie, pull those panties down and show the boys how you play with your pussy."
I sat down on the floor. I slid the bottom of my floral print dress over my panties, which I pulled down to my knees. I reached down, my open legs pointed directly at Bryan to entice him. I rubbed the outside of my pussy with my middle finger a few times, mashing the outside and getting myself horned up. Then I sank my polished middle finger one knuckle deep and began feeling my pussy from the inside.
Bryan looked at me with a purity of lust that I've never seen before or since--like he was a male animal with only one purpose--to copulate with this female and ejaculate inside her.
I squirted some lube into my hand, worked my finger higher up inside. I started moaning from the pleasure of it. Then I switched to two fingers. In a minute, three fingers.
I was really starting to get going now... it felt so good to have my pleasure points hit like that. I looked over--Pete was jerking himself off, slowly. Bryan had his pants down and was ready to fuck. Joe had his hand around Brendan's cock again. Brendan was smiling at me, that devilish smile he gets when he know he's done something naughty.
"We all know you want to do her, Bry. Hop in there and fuck her!"
Bryan came hard-charging at me. He muttered, "I'm gonna fuck this slut" to no one in particular. He grabbed my panties, ripped them over my boots, and sank his dry cock into my lubed-up ass.
I gasped; he didn't even go in slowly. He sank six of his seven thick inches into me in one go. I blacked out, saw stars from the pain.
That wasn't enough for him. He pushed the last inch into me hard. "Fuuuuuck that's tight!" he screamed. Then he started pumping into me, hard and fast. No wonder this guy could never keep a girlfriend.
He panted and groaned for a few minutes as he gave me the least pleasurable fuck I'd ever gotten. He wasn't even looking at me... he was just hate-fucking my hole.
"Turn around, bitch... I wanna fuck you like a dog."
I hopped up, obediently, and turned to show him my ass.
In front of me, Joe was sucking Brendan's fat dick.
Bryan shoved his dick into me in one go, again.
Now he dropped any attempts at being gentle. He speed-fucked me like I was a fleshlight. I couldn't even think I was so ravaged so hard. In retrospect, it's a fucking miracle he didn't hurt me. Maybe it's because my ass had learned to accommodate Brendan and his larger member that I could take Bryan's violent fuck. Whatever the case, he was fucking me brainless.
As he rocketed up the pace, he started screaming: "Fuck. You. Slut. Whore. Fuck. You. Slut..." in rhythm with his pace. The guys were watching him, Joe with Brendan's dick still tucked in his mouth, with concern. When Bryan, that mean, stupid fuck, finally blew his load, I lay there with my face on the ground, sobbing quietly.
Bryan laughed. "Now THAT was a hot fuck."
He must have sensed that no one was going to give him a high-five, because he just walked off to the bathroom alone.
"Jesus, Amie... you alright?" asked Pete.
"Yeah, Petey... I'm fine, thanks. I just need... a minute..."
As I sat there and recovered, Brendan started to moan. Seconds later, he erupted inside Joe's mouth. He shot so much cum it spurted out the sides of his mouth.
Joe looked embarrassed but proud. He caught his first load of cum from a huge dick in view of all of his best friends. There's no going back from that.
I slid my head from off the floor. I grabbed my panties from across the floor, slid them on again over my boots. I could feel Bryan's cum inside my ass, those little fuckers trying to swim inside me, get me pregnant.
Bryan walked back into the room. "So: what are we doing for round 2?"
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What do you think? Drop me a line at sexyamie@hotmail.com if you're turned on.