• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Kasey's Confession Ch. 07

Kasey's Confession Ch. 07

12

Whatever Derek had given me, it lowered my inhibitions and made me very eager to give into my fantasies. The voice inside that told me to run from the situation was getting fainter and while I was somewhat panicked by Mr. Smith's stated intention to "break" me, a larger part of me was intrigued. It wasn't like I hadn't been with men before and it wasn't like I hadn't submitted to them.

I giggled.

"I love making men feel good," I said in a demure, feminine voice.

"That's what I like to hear," smiled Mr. Smith as his hand continued to roam over my exposed ass, occasionally giving it a light squeeze. "You realize that the first time you shaved those legs of yours it was because you wanted men to want you, and not for whatever lame excuse you came up with at the time, don't you?"

"Yes sir."

"And how did you feel when they noticed you in your tight little shorts or your miniskirt and heels?"

"I felt really... sexy."

"I bet you cried the first time you sucked cock, didn't you."

My mind suddenly screamed "GET OUT OF HERE" but my lips trembled and I gasped out, "Yes."

"You cried because your whole life changed in that instant, but you also knew you were always headed in that direction. You were accepting who you are and who you were becoming. You'd fantasized about it for so long in your head but you never told anyone and now your secret was out and the reality was so much better than the fantasies."

"Yes, it was," I gasped.

Mr. Smith removed his hand from my ass and turned to Derek. "Take this bitch in the bathroom and get him ready to get fucked."

Derek led me to the bathroom, where I was flushed out and cleaned, an experience that was embarrassing but somehow arousing. During the experience, Derek didn't speak to me at all until he finished and told me, "It is always good to do that before a date so you'll be ready."

"Thank you, Derek," I said and ran my fingertips along the side of his face.

"Don't thank me," he said with a hint of annoyance. "You're too high right now to realize what I've done to you or what Mr. Smith is planning to do to you."

"He's going to fuck me," I giggled. "I know that."

Derek shook his head and pulled my hand away from his face. "Let's go back to him."

I paused, looked deeply into Derek's eyes and said, "What are you talking about? What is he going to do to me? I've been with a bunch of guys in the past few days and I loved it, so what's the big deal? I want to lose my cherry. I've been fantasizing about it for a long time."

"You aren't thinking straight, Kasey. That's my fault because I dosed you. Mr. Smith takes people like you and me and basically turns them into his slaves. I answered an ad to rent a room when I first came here and that was all I thought it was. Then he found out I was bisexual and liked to wear girl clothes and, well, six months later I'm so desperate to get out that I tricked you into coming here so he'd let me go."

"Why don't you just leave?"

"I don't have time to explain, but you don't just escape. He'll make it fun at first, but then he'll pass you around to all his friends and guys he knows from some website and it just gets worse."

My happy, tingling high that gave me the giggles and made me love touching people and being touched by them was being overcome by a feeling of anxiety and fear. What had I gotten myself into?

"Help me," I whispered, now terrified that Mr. Smith would hear us talking.

Derek pulled me into the back corner of the bathroom and told me, "Don't consent to what he asks you or tells you to do. Refuse to comply. He'll get pissed off and yell at you and tell you to stop fighting and that this is what you want, but stand your ground. He'll get frustrated and mad and yell and maybe even get physical, but he won't take you against your will."

"I don't know if I can—"

"It is up to you, Kasey. Resist and he'll tell you what a rotten cock tease you are and how you are worthless and pathetic, but he'll send you home. Give in and he'll own your ass until you find him someone new to play with."

I could feel my heart racing and my body trembling; I was frightened of the prospect of going back out into the living room and facing Mr. Smith.

Derek took my hand and told me, "Be strong and remember what I said. Once he gives up on you he'll tell me to take you home."

"I'm not strong," I said, starting to cry. "I'm a total wimp."

"You're not a wimp," Derek said as he looked into my eyes. "It took courage to walk through the mall in those shorts. It took courage to walk up to me and give me your phone number. I couldn't have done either of those things. I hide who I am and Mr. Smith uses that to control me. You are a lot stronger than you think you are."

I walked back out to the living room, wearing only my pink thong panties, a t-shirt and my pink heels. Mr. Smith was relaxing on the couch, drinking what appeared to be whiskey with ice cubes. He barely reacted to my return, his face buried in a magazine, but when Derek announced that I had been "properly prepared" he looked up at me and smiled.

"I want to go home," I blurted out.

"Well, Dorothy," Mr. Smith snickered, "you're not in Kansas anymore."

"I am not interested in sex with you," I said, struggling to form words that made sense, but as I did they came out painfully slow and in a hoarse, off-key monotone.

"Oh, really now," said Mr. Smith, laughing at me. "Look at you, standing in front of me in high heels and those slutty panties with your smooth little ass on display after you just let my twinkie get it ready for me... and now you're not interested in sex?"

"No sir, I want to go home."

Mr. Smith laughed heartily. "Kasey, you are prancing around in front of us wearing nothing but a pair of pink thong panties whining about wanting to go home. How stupid do you think I am?"

"I don't think you're stupid, sir. I thought I was coming here to see Derek and hang out with him. If I made a mistake, then I am the stupid one, sir."

"You want to 'hang out' with Derek? Is that what you want, sissy? Well, then get over there and get down on your knees in front of him and 'hang out' if that's what you want."

I looked over to see that Derek had quietly taken off all his clothes while my attention was fixated on Mr. Smith. He had a boyish body and his skin was completely smooth all over, including around his genitals, which were very much on the small side despite Derek's very hard penis.

"What does Kasey look like to you, Derek?" Mr. Smith asked.

Derek sat, frozen in silence until Mr. Smith snapped at him. "I'm sorry Kasey, but you look like a slut that needs discipline."

"Go ahead and stroke yourself," Mr. Smith told Derek. "You know Kasey didn't come over here to do anything other than tease you, don't you? He won't even get on his knees for you."

"I know," Derek muttered as he started stroking his cock.

"No... I didn't mean to—"

"Shut up," Mr. Smith snapped at me. "Don't speak unless I tell you to, cock tease. You don't even know what you want. I bet you've been hooking up with men left and right because you can't get enough cock, and now you come over here wanting to mess with my houseboy's head."

I was about to defend myself when I stopped and remained silent, feeling a powerful compulsion to avoid offending Mr. Smith. He got up and turned me so that my ass, still exposed by the fact that I was only wearing my thong panties, towards the masturbating Derek.

"Let me change into something more comfortable," Mr. Smith said and walked away. He went into his bedroom and closed the door.

As soon as the door closed, I knelt down next to Derek, not to give him head but to whisper to him. "This is our chance, let's get out of here."

"Prove to me you aren't just a tease and a bitch," Derek said, grabbing my arm. "Suck my dick."

"Take me back to my place and I promise I'll give you the best blowjob ever. Please, help me, you said you would."

"Just a little taste... for now, please, Kasey, show me you want me."

"He'll be back soon, though," I said as I moved closer and took his cock in my hand once his hand moved away.

"He's on the phone calling his buddies," Derek said with a moan. "It will take him a while. Just get me started..."

My heart was pounding and I was incredibly nervous but at the same time felt relaxed and my body was tingling in the most pleasant way. I knew it was the drugs, but I couldn't shake myself out of the high, so I leaned in closer until I had Derek's cock inches from my face.

The words came out of me uncontrollably, and as soon as I spoke them I recoiled in horror.

"My gosh, it is so small," I said.

"You fucking bitch," Derek yelled and pushed me off him angrily.

Mr. Smith opened his door and stepped out into the living room looking amused. He was wearing a blue bathrobe and carrying a portable phone.

"Is there is problem, girls? Are we not playing nice?"

"Kasey said my dick was too small for him," Derek told him. "And she wanted me to help her run away."

"Oh my," said Mr. Smith, who then walked over to Derek and tousled his hair. "You always think some prince or princess is going to show up and make all your dreams come true. I think they would call you a hopeless romantic, but I think you know the truth about people, don't you, twinkie? All they want is what they want and the only reason they pretend to care about you is so they can use you."

"I didn't mean it," I whimpered, still on my knees. "That isn't what I meant..."

"Does this meet your high standards, slut?" Mr. Smith asked as he opened his robe and turned towards me, showing an enormous cock that was fully erect and covered with thick veins which appeared to be pulsating.

"Oh shit," I said, the words spilling uncontrollably out of my mouth, "you have an incredibly gorgeous, beautiful, amazing COCK!"

Any self-control I had was melting away as I found myself drooling and staring at Mr. Smith gigantic throbbing cock, which only seemed to get bigger and thicker the more I looked at it.

Derek sat with his arms crossed, looking completely disgusted. I barely even noticed he was there now that I felt hypnotized by what I could not look away from. I was crawling towards Mr. Smith, on my knees, visibly drooling and panting.

Mr. Smith held out his arm, his hand making the sign to "stop" just as I got within arm's reach of him. He turned towards Derek.

"You can feel free to pack up your stuff and hit the road," he told Derek. "I think Kasey will enjoy what I have in mind for him."

"I would like... to watch," Derek said, breathing heavily as he watched how I obediently knelt at Mr. Smith's feet and gazed lustfully at his erection.

"Why don't we all sit down and relax," said Mr. Smith, pulling his robe closed and concealing his cock from my hungry eyes and mouth. He produced what appeared to be a large joint from the pocket of his bathrobe and motioned for me to sit down on the couch. After I got up from the floor and sat down, crossing my legs as I did so, Mr. Smith sat down next to me while Derek took up residence in the large black recliner across from us.

After the joint was lit and had been passed back and forth a few times, I felt Mr. Smith's hand on my thigh. His touch felt wonderful and I felt like I was going to melt from his increasing attention. When he spoke to me, I listened intently, but when he started talking to Derek my attention wandered, distracted by sound and light and various things that decorated the room around me.

"Do you ever wonder why you have so much fight in you?" Mr. Smith asked, abruptly pulling me out of the daze I was in. "Do you ever ask yourself why, when you want something so badly, you have this part of you that always wants to run away?"

"I'm scared," I said as I took another hit off the joint. "I'm so scared of what I want because it isn't just hooking up with an occasional guy. I think I could almost deal with that, but..."

"But you want to be forced to submit to men every day, and not just every day but morning, afternoon and night. Am I right, Kasey?"

"Yes," I sighed as his hand ran gently up and down my thigh and then directed my hand inside the folds of his robe to where his cock was waiting for me.

"You're a princess, Kasey, and I'm going to treat you like one," he whispered into my ear. "You are a prize. You are a trophy and I want to show you off."

"Really?" I asked as I looked down at his cock just as my hand drew it out of the robe.

"Oh yes, Kasey, you look so beautiful all dressed up, especially with those high heels and those long legs. I want to show you off to all my friends."

"You really think so?" I asked and stretched my legs out in front of me to look at them all the way down to my pink toenails.

"Of course I do, Kasey, but I don't want to just show off how sexy you are. I want to show off your sexual talents to all my friends as well. Of course, I want to see just how talented you are so I can tell them all about your amazing skills. Why don't you slide down there on your knees in front of me and show me how you suck a cock."

From the very first time that I went down on a man, the thing I love the most about it was how alive a cock felt when it was hard. It was warm, soft and so unlike anything else I'd ever held or tasted. After my first experience, I was hooked, and while I was so reluctant to admit it, I could not deny that I was absolutely and totally in love with cock.

Once I was on my knees in front of Mr. Smith, still holding onto his amazing cock, I stared longingly at it and then looked up at him and smiled. Then I leaned in and ran my tongue slowly across his balls and then up the powerful veiny shaft of his cock up to the head. My tongue flicked lightly at the underside of his cock head and then I rang my tongue around the edge of it while a slow and honest sound of delight seeped out of me.

In retrospect I believe I would not have been so reluctant to give into my desires and, dare I say it, my need, if I could have come out to people I knew as being gay. I didn't want to date men. I didn't want to have a "boyfriend" and I didn't want to pursue any kind of regular relationship with a man. What I wanted was cock, as much as I could get and as often as possible. I wanted to dress sexy and show off my legs, which even women said were so nice they wished they had legs like mine. I loved being lusted after in my short shorts and in my miniskirts and high heels. Giving in to Mr. Smith, knowing how he planned to share me with his friends and use me for his pleasure, only made my desire grow stronger.

"I want to submit to you completely," I said before sliding the head of his cock into my mouth.

Mr. Smith smiled and ran his fingers through my hair before gently pulling my head down. Derek had moved over to sit on the arm of the couch, watching closely while stroking himself.

When people talk about finding their true love and having that first kiss that set off emotions they'd never felt before, I always think about the first time I felt the head of a hard cock between my lips. The powerful but sensitive texture of it as it passed between my lips and my tongue ran over it as it slid deeper into my mouth and rubbed along the roof of my mouth and down into my throat, I felt myself falling in love.

Mr. Smith's cock was filling my mouth, and I wrapped my lips tightly along his thick, veiny shaft as it slipped deeper into me until it found my throat. I gagged slightly, looked up at Mr. Smith for his reaction, and then slowly moved my head up, working his shaft with my lips and tongue as I did so.

I felt myself writhing in total ecstasy as my head bobbed up and down on Mr. Smith's cock, moving not only up and down but moving ever so slightly around and around as I sucked him.

Then he lifted my head up and off his cock, looked into my eyes and said, "I want that ass, that sweet virgin ass..."

I felt so happy my smile stretched from one ear to the other, especially after I stood up and looked down at my legs and slowly slid my thong panties down my thighs, my calves, and then over my high heeled shoes and off completely.

Mr. Smith sat me down on the couch and then leaned me back so I was lying face up. He removed his robe and went to the paper bag he'd brought with him when he arrived. He pulled a condom out of the bag and quickly pulled it on over his hard cock. He covered it with some kind of lubricating jelly. Then he came back to the couch and positioned himself between my legs. He took hold of my legs by gripping them behind the knee and pushed them back so my feet were over my head and apart.

I felt the head of his cock press against my asshole. He pushed slowly back and forth against it until quite suddenly his cock head popped into my asshole. He let out a sigh almost as loud as the one I released and pushed his cock hard into me. It sank into me slowly, and I could feel every inch taking me as he continued pushing relentlessly until every last inch of his massive cock was inside me.

I moaned loudly and without pause throughout his first penetration. Although it did hurt, and it hurt more than I imagined it would, it felt so good and so right. I uncontrollably turned towards my left leg and started kissing it while I continued moaning.

And then Mr. Smith started pulling out of me. My moaning got louder to the point I was all but screaming. And when he had pulled back as far as he could without withdrawing completely he pushed it into me again. He continued pushing in and pulling out over and over until my ass had gotten used to his very welcome intrusion and he was able to move back and forth inside me with relative ease. Every few thrusts or so, my ass would suddenly tighten and clench around his cock and then release it, and soon that became my favorite part of my first anal experience.

At some point early in Mr. Smith's thrusting, I felt a warm liquid splash across my face. Derek, who had been watching and had taken roost on the arm of the sofa by my head, had stroked himself to orgasm and shot his load on my face.

All I could do was turn and look at him, my mouth agape, moaning loudly as Mr. Smith started pounding me harder and harder with every thrust.

"You deserve what's coming to you, slut," Derek said, sounding both angry and disappointed.

Derek walked away. He grabbed his clothes off the floor, then went into a bedroom and closed the door behind him.

I turned my head back and looked up at Mr. Smith, smiling and groaning as he fucked me, holding me down with one leg pushed up against the back of the couch and the other flailing about wildly out over the coffee table. I couldn't believe how good I felt. The pain seemed to have melted away into a fog of ecstasy. I reached up and grabbed hold of Mr. Smith's powerful biceps and watched his face twisting in a way that told me he was thoroughly enjoying fucking me.

As much as sucking cock had been a revelation on the level of falling in love for the first time, this was ten times better. I could feel tears streaming down the sides of my face and my moans were very loud, but I couldn't control or stop either.

My legs started shaking and I reached down to feel my dick, expecting it to be hard but finding it completely and utterly limp. Yet, I felt like my body did whenever I reached orgasm. It was better than my usual orgasm, as my whole body seemed to be in the throes of ecstasy, but at the same time the final release seemed so distant and unobtainable.

"Fuck me," I started yelling between my loud moans. "FUCK me!"

He started slamming me harder and I felt the hugeness of his cock filling me and alternatively pushing me open and then letting me close just to be opened again. My body twitched and seized, hanging on the edge of orgasm for what felt like forever before my entire body erupted.

12
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Kasey's Confession Ch. 07

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 21 milliseconds