The TGirl Academy

"Should I come back?" I asked.

"No. this bloke fancied himself straight and was up for me to blow but he was getting grabby and a wee misogynistic so I decided to go from licking his cock to licking his arse, and Robert liked it, didn't you Robert?" She said through her groans.

"Yes baby, I loved you licking my ass, and I love you fucking me," he moaned.

Kelley was on top of him pounding away. Robert was face down on the bed. Suddenly Kelley stopped and gestured Robert to follow as she sat on the edge of the bed and positioned Robert into reverse cowgirl. Robert's dick was massively thick and ridged with prominent veins sticking out, more than I had ever seen. He was ramrod hard at about nine and a half think inches. His cock bounced beautifully as he rode up and down on Kelley. I took out my now hard cock and started stroking.

My nipples had been getting sensitive and I felt them rubbing under my fake tits and it spurred a good amount of pre-cum out and rubbed it all over the head of my cock. What was strange however was even though that beautiful cock was presented before me and at the ready I was holding back. I'm a size queen and consider myself a bit of a slut but I just watched and stroked, knowing I was not allowed to cum.

Kelley reached around and grabbed Robert's cock and started stroking it fast and hard. Robert was losing his mind.

"Let's go stud, let's have a bit of a blow, yes?" Kelley said.

"Oh, yes, oh fuck, oh fuuuuuuuuuucccccccckkkkkkk!" Robert yelled.

The first massive shot exploded over Robert's shoulder and splashed Kelley. She liked that.

"Oh good bye Robert," she said.

Then the next shot hit Robert on his neck then two on his chest and then a few more small spurts on his stomach.

"Oh fuck, so good, so good, yessssssss," Robert moaned.

Then Kelley shoved Robert off and rolled her head and eyes back as she came again and again.

"Ah, ah, ahhh, cuuuuummminnggg, ahh, yeah, baby!" she screamed.

It was amazing to watch her cum without touching herself. Her dick bobbed on its own and in different directions with each shot. She didn't cum as much as Robert but her shots did reach her chest, soaking her top. Robert stuck his cock in her mouth and Katey mewed and sucked on it for a bit. She finally spat his half hard cock out and looked him in the eye.

"Now Robert, I know you consider yourself straight and my understanding is the entire kitchen staff is also but I want you to make a go of polishing off a buddy's knob today, can you do that for me stud?" she said and blinked her eyes and twirled her hair for him.

He nodded and she spanked his butt before he dressed and went on his way. Katey circled me as I desperately stroked my cock. It was squishing with noise now there was so much pre-cum. I was so desperate to cum but we had more classes to get to so I tucked my hard on down through the bottom of my red silk panties, put on my skirt and went to class.

My mind was foggy all day; I was lost in a sea of lust. I was a size queen and I passed up Robert's cock to hold out for Luis' smaller one? I was wondering if it was the hormones at work. I also hoped the hormones weren't going to lead to me wanting to be monogamous, after all I had decided to become a woman so I could be promiscuous.

Later that night as I went to sleep while edging myself I finally came up with a plan to have wonderful Luis finally give me some relief.

Luis was clearly happy to see me on his next shift. He remarked that I got more and more beautiful each time and that I was losing weight. I was actually. The hormones had broken down much of my muscle mass in my chest and my legs were also turning more girlish and had stopped growing hair which was a nice side effect.

I found myself giddy and kissed him long and hard and I felt his cock stiffen through his khakis. We broke the kiss and kept our faces close, both in heat.

"You make me so hot Tiffany. I know what I'm doing is wrong but I can't help myself. But you must be so disappointed in me," he said, suddenly looking sad but cute.

"Frustrated is much different than disappointed. I dream about your wonderful dick and all the cum it gives me, truth be told." I said.

"I dream about you sometimes too," he said.

"Luis, you know I'm having breast work and pussy work down here and you've been a good boy to avoid them, but have you ever fucked your girlfriend's ass?"

"No, she gets all mad and stuff when I try," he said.

"Well baby doll, I want your wonderful hard cock in my ass, can you do that for me Luis, baby doll?" I think I actually purred.

"I can, it's just, you know..."

I did know. That's why I reached out my hand.

"Luis I'm going to give you my pretty little ass but on two conditions. One, give me your truck keys.

He handed them over and I dropped them down my T-shirt into my fake cleavage which made him feel even more they were real.

"And two, you give me just sixty seconds after you cum, can you promise me that Luis?"

"Sixty seconds?" he asked.

"Yes, after you cum, and you will, I want you to count out sixty seconds out loud and then if you need to runaway for whatever reason you do then you can but I need you to promise me sixty seconds. Can you do that Luis?"

He nodded and or gulped. I urged him to take his cock out carefully as I knew it was already hard and ready. I reached into my purse - yes I was carrying purses now - Luis Viton if you must know, and pulled out some lube. I let him know I would lube myself not his cock so he could last long enough to get inside me. I flirted with him over my shoulder as I greased up my hole. My ten inches of man meat was side strapped to my leg out of view but it was rock hard.

Then I leaned both arms against a tree and presented my ass to him. He slipped one finger in and a mewled with delight. He wasn't interested in playing though; he was just gauging his target. He stepped up and pressed the head against my hole.

"OH Tiffany, your ass, it's so tight, I can't believe I'm about to fuck you," he said, sweet thing.

Then he popped past the outer ring and got just a little past his head in when suddenly:

"Fuckkkkk, oh, cooooommmiiinngggg, oh Tifffany, oh, your ass, aaaaaaaaaaahhhhhhhhhhhh!"

He was squirting so much I couldn't believe it; it was just filling me so deep with squirt after squirt. I moaned and kept as quiet as I could as my own cock shot off straight down at the ground. I was hoping if he saw it he would think it was his overflow. I muffled a scream into my arm as I came.

But then sure enough he froze and I knew he was about to bolt so I surprised both of us when I yelled out.

"Luis put your god dammed cock in my ass RIGHT NOW and count to sixty!"

He was shocked at my outburst and hissed as he pushed all the way until I felt his balls on my ass. He stayed frozen there and was grimacing about it being too sensitive so I demanded again he start counting.

He didn't move but he did start counting. By the time to get to twenty five I felt his cock twitching. It had never gotten soft. His counting stopped and his breathing quickened.

"Oh shit Tiffany, this feels so good, your ass is so tight. Can I fuck you?"

"Please baby," I begged.

He pulled out slowly and then back in again, groaning with delight. He did this slowly a few more times and then suddenly he growled.

"Oh your ass is fucking tight. You're such a naughty slut to want it in your ass aren't you bitch!" he stated rather than asked.

"Yes, I want to be a good slut for your hard cock," I replied.

He smacked my ass very hard several times and I squealed in delight.

"Yes, I'm going to tear this beautiful little slut ass up," he growled.

He started to pound me so hard, one of the harder more relentless fucks I have ever had besides Tree and Mistress. He was pounding and slapping my ass and calling me names and groaning and just outright fucking the shit out of me and I loved every minute of it. My cock was hard again but I didn't care. I was feeling the pressure build in my ass and my breathing hitched and then I couldn't hold it.

"Ah Luis, you're making me cum, baby, you're making me... Aaaaaaaaarggghhhhh, ah, yes, yes, yes!!"

My cock stayed hard, I had actually just cum in my ass like I did with mistress. It was so good, so different, and so unique; it's all I ever wanted. I was murmuring my appreciation to Luis but he just kept calling me a bitch until suddenly I felt him falter slightly and one of his legs seemed to shudder.

"I think, I think, oh, it's going to, oh, this is different, oh, my, oh baby, oh you filthy bitch, oh, it's, oooooooooohhhhhhhh, ffffffuuuuuuuuuccccckkkkiiiinnnnnggg hhhheeeeeeeelllll, yeeeeeaaaaahhh, ahhh, nnnnnnnnn, it's so fucking goooooooddddd!"

He was losing his mind and squirting another load in my ass. I was soaked as it was pouring out of my ass. To my surprise he kept up with the fucking for a few moments and then finally he pulled out and grabbed me and kissed me so deep. I reached down and stroked his cock while we kissed. It was softening some and he was groaning and shaking in sensitivity while I played with it.

When we broke the kiss he stared into my eyes.

"I never, ever in my life, felt like that before. I've never had an orgasm feel so good, God you are beautiful."

"Honey, it's because your first orgasms have been about need not pleasure. When you hung in for round two, that's for pleasure, that's how it can always feel if you work on it," I kissed him again.

"I will work on it. I'm always so sensitive after and ashamed at how quick, that's why I always run away, plus feeling guilty about my girlfriend, and..."

"Do you love her Luis?"

He seemed not to want to answer but nodded.

"But if I keep offering my ass you'll take me up on it?"

"I can't resist you, you are so beautiful," he said.

"For a bitch, right?"

He reddened, looked down.

"Sorry about that," he said.

I lifted his chin.

"Do not be sorry, it made me cum in my ass Luis, that's special, that doesn't happen every day," I said.

"It doesn't?"

"You really do think I'm a slut don't you?"

"I think you're an angel, but..."

"You already have an angel?"

He nodded his head then we both smiled sadly and held hands.

"Goodbye Luis," I said and stepped backwards.

"Goodbye Angel," he said.

I kept walking backwards but he wasn't moving, though normally he was so quick to get out of there.

"This is the part where you walk away so you don't see me cry," I said.

"My keys," he said.

I turned red, embarrassed, starting groping at my chest, couldn't find them, feeling awkward, then he looked over and reached down to pick them up from the ground by the tree.

"I guess you fucked them out of me," I said.

"I guess I did Angel, I guess I did," then he flashed that gorgeous smile and drove away.

I turned back towards the school and as I walked I cried. I cried because my heart was breaking, I cried because my body was changing, I cried because I missed my friends, but most of all I cried because for the first time in my life I was fucked by someone who believed I was a woman. I cried because I had finally gotten relief and that beautiful Luis had fucked me so well. He was my first as a woman, that's why I had been holding out for him.

But now that my virginity was over I was not going to be monogamous, I was ready to fuck the world!