Big Hard Girls
Page 5
“I said, get on the bed,” the man said to Terry. He was standing naked, with his cock throbbing and nearly touching his sternum. That erection was intended for Terry’s asshole. And if Terry let it in, there may be no turning back. How could he turn back after losing his anal virginity? What else would he have to lose at that point? As long as Terry had something to lose, he still had his pride and his sanity. But if he let it all go, then there were no limits to his new illness.
CHAPTER XI
Terry’s whole body was trembling as he lay himself down on that bed, on his stomach. He tried to take a deep breath in as his client climbed on top of him and bent over to rub Terry’s back. Terry could feel the man’s hard cock throbbing on his ass, warm and large, taking a short break after nearly being stimulated to orgasm by Terry’s soft lips.
Terry closed his eyes and tried to stop his head from spinning. He didn’t care about the five hundred dollars. He wasn’t doing it for the money—and that’s what scared him more than anything. He was just doing this for the excitement. Had the man pulled up and said, ‘I’ve got no money but I want to fuck you anyway,” Terry would have probably still gotten into the car.
He could hear the man slipping a rubber onto his cock. He was surprised they made rubbers that big. Then he heard the squirting of lubricant as the man got his long hard cock ready. Terry tried again to take a deep breath, and this time he got a bit of air into his trembling lungs.
Terry found himself thinking about his friends and family members—wondering what they would think if they knew what Terry had been doing over the past week, wondering what they would think if they could see him now, all dolled up and about to take a cock in the ass. And to think, this all started because of a moment of drunken shenanigans. Was this degeneracy always lying dormant? Did everyone have this in them, or was Terry just a special degenerate?
Terry felt the man pulling his panties aside a moment before the tip of his warm, lubricated penis pressed against his puckering hole. It felt impossibly enormous, yet Terry just remained still, allowing the man to carry on. What if his penis was so big it ripped Terry apart? What if it permanently stretched him out and he had to wear diapers for the rest of his life? What if it hurt so bad that Terry left that apartment with PTSD? Why wasn’t Terry stopping the man?
He started pressing that hard cock in. The pressure was intense as he tried to get that initial penetration. Terry bit down on a pillow as that tip finally pressed through, rattling his ass. “Oh God,” Terry moaned. His fingertips dug into the sheets and his legs squirmed—but the man had him pinned, and the man wasn’t stopping. He sunk his cock in deeper—just another inch deeper, but it was enough to make Terry tense up and squirm even more.
“Do you like it, slut?” the man asked.
“Yeah,” Terry said, and he was shocked to hear the word leave his tongue.
The man sunk another inch deeper, making Terry even tenser, making him moan louder. There was a real cock in his ass: the cock of a stranger—a cock that could have been in many assholes before Terry’s. He could feel it throbbing. He could feel the man’s veins pumping blood.
“Please be gentle,” Terry managed to say. But the man only replied with a chuckle. That cock sunk deeper. It was now deeper than that black steamer handle had ever gone. It was deeper than the steamer handle could go. And the man still had a few inches left to play with. He sunk in a bit deeper.
Jolts of warm energy were pulsing through Terry’s body. His hands were twitching and his eyes were flashing. He moaned and squirmed and then he started to feel it: the euphoria. The man had found his sweet spot, and his giant cock was pressing hard into it. A bit of drool formed on the corner of Terry’s lips. He fought back the urge to moan and let the man know that he was suddenly enjoying the stuffing.
The man sunk in deeper with a final shove, pressing his pelvis into Terry’s ass. Terry could feel the tip of the man’s cock pressing up to his sternum. He could feel every throbbing inch of the impressive member inside of his body. He turned his head in an attempt to fight away the urge to moan, and that’s when he saw the mirror: his own reflection staring back at him.
And Terry realized he wasn’t submitting to degeneracy. Dressing up in pretty clothes wasn’t just some sick addiction, or some mental illness. He looked good as a girl. His face was stunning with a bit of makeup, and that skimpy blue dress gave him curves worth of a magazine cover. He hadn’t discovered some dark secret about himself when he first tried on those clothes—he discovered something amazing about himself. He discovered that he had a woman inside of him. He discovered that he was happy wearing pretty clothes and cute makeup.
Now, he was happy that he put on those clothes as a joke a week before. If he hadn’t, he wouldn’t have had one of the most fun weeks of his life. He would be in that apartment now, making five hundred dollars for having a ton of fun and getting off. He wouldn’t have experienced being catcalled on the street, and he wouldn’t have gotten free drinks at the club. He had so much left to experience as a woman—and this rich stranger was just a small part of that amazing experience.
So Terry let his body relaxed. He continued watching his reflection as the man started to thrust in and out. He watched as that long cock rose up and disappeared, over and over, sinking deep inside of him. He watched as his long beautiful hair bounced, and he watched as his big eyes glowed. He was watching himself, in his element, with a big warm smile on his face—on her face. She wasn’t a man in those clothes. She wasn’t a man with that makeup and that wig. And in his heart he wasn’t a man either.
The client grabbed her hips firmly and pounded his cock down with force. His pelvis slammed her butt, making it ripple, making jolts of warm euphoria burst through her whole body. She didn’t want the moment to end. She wanted that big cock inside of her all night long. And maybe she would offer the man a discount for a second fucking in just an hour or so…
“You’re so fucking tight,” the man groaned through clenched teeth. His hair was ruffled on his face, and beads of sweat were running down to his chin. “And fuck, I’m so hard. It feels so good.” Terry liked it—she liked making the man happy, even though she didn’t know who the man was. She liked that she was sexy enough to make a man so hard. And she didn’t blame the man. Looking in the mirror, she was arousing herself.
She groaned and squirmed and then felt a warmth pooling around her cock. “Oh God,” she moaned. “I’m coming. You’re making me come.” The man shoved his hand down, underneath Terry’s cock. He cupped the tip of her cock and grabbed a few blasts of her amazing cumshot. Then he brought that hand to her lips and made her lick it up, which she did without hesitation. He wiped some of that cum on her cheek and then he grabbed her hips again so he could drive his cock in harder.
And he didn’t last much longer. After just a few more pumps, he was filling that condom with his hot load. He groaned and held her tight until he was depleted, and then he fell back onto the bed. Terry stayed in place, catching her own breath, even though she hadn’t done anything but lay in place. Her asshole was a bit sore but the euphoria was still teeming through her body.
The man paid another two hundred to have her stick around for another hour. It was only twenty minutes later when his cock was back in her ass, pumping her to another orgasm. When Terry finally returned to her apartment that night, she found herself staring at the seven hundred dollars for a minute before turning her gaze to the mirror. Even after everything, she still couldn’t get over how beautiful she was—and how beautiful she would be from now on.
She didn’t work on Sundays, so she spent the whole next day at the mall, buying a new wardrobe with the money from her paid romp. She didn’t plan on pursuing the life of a prostitute—that was just for fun, just for the experience. But she did plan on pursuing a new life as a woman.
She knew there would be some embarrassing moments, especially at first. She knew there would be some weird looks from the usual clients who knew Terry—and not to m
ention friends and family members. But she knew that the awkward phase was just that: a phase.
When she woke up that Monday morning, ready for the busiest day of the week, she knew that the hardest part of the day was going to be leaving her apartment, allowing her neighbours to see her in a dress and a pair of heels. She knew that it would be awkward when the first usual client came into the store, but she knew it would only get easier with each passing minute, with each passing hour, and with each passing day. She was ready—because sometimes it takes a bit of being uncomfortable to be able to truly appreciate the good things in life.
THE END
THROBBING LESSON
Jake is doing great in all of his senior year classes, except for one: Miss Barrett’s English class. She’s been extra tough on him ever since he started that cheeky rumour that she was actually a tranny. Now, with just three months of school left, if Jake doesn’t pass her class, he won’t be going to college.
So when he’s caught cheating on an assignment, he thinks it’s all over for him. He begs Miss Barrett to spare him, and then her eyes light up with a fun idea, involving short skirts, cute heels, a bit of eyeliner, and a new, promiscuous persona.
CHAPTER I
Miss Barrett hated me. She’d had it out for me ever since I spread the rumour that she was a tranny, but that was her own fault for failing me on a test that I should have passed.
And it’s not like she looked like a tranny. She was probably the hottest teacher in the school—forty-two years young, perky tits, long smooth legs that were never burdened by pants or even pantyhose. In fact, I always had a big crush on her, until she failed me on that test.
She was a hard ass with a hard ass. If a student submitted a report with more than ten typos, it was an instant fail. She had the same rule with her tests—if written answers had a certain number of typos, it didn’t matter if the answer was right. That’s how I failed that damned test—but it really wasn’t fair. I spent the same word wrong in four places; surely that should only count as a single typo. If anything, it was her fault that I failed because she never taught me how to write that word properly… I think the word was ‘calendar.’ And I wouldn’t have been so mad if it wasn’t the biggest test before we got our report cards before the Christmas break. I had to show that report card to my parents, and then I had to suffer through a Christmas of scorn, being told I would only get that new PlayStation once I got my grades up. Bullshit, if you ask me.
So yeah, I told all of my friends that Miss Barrett was a tranny. I told them that I was walking by her classroom after hours and I saw her adjusting her skirt. It wasn’t true—it was just the meanest thing I could think of. It was a little bit of harmless revenge. It was only a couple of days before every kid in school had adopted the gossip. My own friend, Terrance, came up to me and said, “Did you hear that Miss Barrett used to be a man?”
I was brought into the principal’s office. They asked me, “Did you start this rumour about Miss Barrett?” and of course I denied, denied, denied. That’s what you have to do when you’ve been accused—just deny every claim. They had no proof that I said it, even if my friends ratted me out. I got two weeks of detention, in Miss Barrett’s classroom. And it was the worst two weeks of my life: one hour after school, every day. She took away my phone and she told me to sit silently. She didn’t even give me work to do, and she didn’t let me do my homework. “You can do that when you get home,” she would say. But I wouldn’t get home until dinnertime, and then my parents would make me help with the dishes, and then that only left a few hours before my bedtime. So those two weeks were completely ruined.
I was on my best behaviour for the next few months. I didn’t want to suffer through that nonsense again, though I didn’t forget about that failed test. I was still convinced that I not only passed it, but that I’d come pretty damn close to acing it. Sure, dock a few points for each typo—but fail me completely? How could I ever let that go, especially since it was just a couple of months before I sent out my college applications?
And she never forgot about the tranny rumour, even though it was never officially proven that I started the rumour. She would glare at me during class, and she would always call on me whenever she asked the class a question. She would make me stand up. Sometimes she would make me stand at the front of the class so that she could tell me that my answer was wrong. She was determined to humiliate me, for a bit of revenge of her own. An eye for an eye leaves the whole world blind, I guess.
She dinged me with detentions whenever she could. She would time me when I went to the bathroom. One afternoon I spent six minutes in the bathroom when I was only allowed five—and of course that got me an afternoon of detention. And she was ruthless—I was five minutes late for class one morning, and when I came in, I discovered I only had five minutes to complete a pop quiz, which she took her sweet time handing to me. She didn’t stop the clock while I fished my pencil out from my bag, but I swear she ended the quiz before the full ten minutes had passed. I failed the quiz, and guess what? The punishment for failing was an afternoon of detention.
I was almost starting to think that she enjoyed my company. Why else would she look for every reason to keep me in her classroom after hours? Maybe so she could bask in my torment… She would always sit behind her desk and stare at me with a big grin. She knew there were so many more things I wanted to be doing. She knew that my friends were all out, having fun. She knew that my parents were scorning me every time I got home from her damned detentions. And she loved it.
I wanted to get back at her, but I didn’t know how. I didn’t want to risk ruining my college aspirations for the sake of revenge. My friends kept telling me to let it go. Terrance snapped a picture of me while I was ranting about Miss Barrett. He turned his phone to me and I saw what my friends saw: red face, lips pressed thin, dark, brooding eyes…
I turned eighteen a few months before graduation, and someone passed the memo along to Miss Barrett. She started tormenting me in a new way—with her soft, tight, and perfect body.
The worst humiliation she ever tormented me with was on an early February morning. She was wearing a white blouse that seemed to be tighter than usual. She had her two top buttons undone, with the heat turned up in her classroom. It was presentation day, but she gave us all ten minutes to prepare for our presentations. I had a report on the novel, 1984. I was going to present a slideshow that I made on the computer, which I had ready on a thumb drive.
Miss Barrett came up beside me and she leaned over my desk. I could see down her top. I could see her lacy red bra and the curve of her mouth-watering titties. She was wearing perfume. I’m not sure she’d ever worn perfume in class before. “Are you ready for your presentation?” she whispered into my ear in a voice that made my head spin.
I may have hated her, but goddamnit, she was hot. I wanted to reach up and squeeze those tits. I wanted to bury my face in them. And she wouldn’t go away. “Where is your presentation?” she asked, still using that tantalizing voice.
“On this drive,” I said.
She reached across the desk and gently fingered my thumb drive. “This drive?” she asked. Her tits were closer to my face than ever. That perfume smelled amazing. And I could almost see her nipples—she just had to bend over a touch more.
“Yeah, that one,” I said, my voice cracking.
She slipped a hand gently onto my back and she rubbed. “I hope it’s a good one,” she said. My legs trembled. My cock was suddenly hard, pressing tightly against my pants. She kept rubbing her hand in small circles, making my head spin faster and faster. The tips of her fingernails were teasing my skin gently. “Can I see your stick?” She reached over and grabbed the thumb drive. My heart stuttered.
And then she stood up straight and made an announcement to the class. “Let’s start our presentations. Jake is going to start. Go ahead Jake. Go up to the front of the classroom.” She took my thumb drive to her computer. But I couldn’t stand up. My heart was pound
ing ferociously and I had the biggest erection I’d ever had in my life—and I had nothing to hide it.
“Jake?” she said, booting my presentation up on the projector. “Your presentation—you can start now. Come on up.” She had a smirk on her face. She knew what she did. “If you don’t get up now, I’ll have to fail you. Don’t be shy.” So I had to decide: take another fail, or let the whole class see that I had an erection. But I couldn’t take another fail. If I took another fail, then I wouldn’t have the grades to get into any decent college. I had to stand up. I had to face my classmates with a raging boner.
I tried tucking it in my waistband, but that only gave me ten seconds of safety. I felt my shirt riding up and I ended up pulling up my pants, worried the class would see the tip of my dick. But when I yanked up, my cock was released from my waistband, and everyone saw my erect bulge.
Everyone laughed. No one heard any part of my red-faced presentation. They just laughed and laughed. And Miss Barrett sat behind her desk with a big smirk on her face. My heart fluttered into my stomach and it was days before I was able to look anyone in the eye again.
CHAPTER II
It was a month later when I found myself in her classroom after hours once again, with a two-hour detention. This time, I didn’t even understand why I got the detention, but I fought the urge to fight it, worried she would dock my final grade. I was already on the cusp on dropping below the minimum requirement for most of my preferred colleges.