Becoming a Whore

I gradually picked up the pace, sliding the dildo in and out of my ass until my pain gave way to pleasure. My sobs of pain became moans of pleasure. If Craig didn't want me, screw him, I'd find someone else to pump me full of his seed.

I came twice that night while pumping my ass and then passed out exhausted in the shower. I wasn't satisfied but my hunger was slacked at least.

I decided to go out the following night and see if I could find myself another man. I dressed up in my usual outfit and left the apartment around one in the morning. I left the trenchcoat behind. I was feeling better about myself, more confident. This morning I hadn't even needed to use a lot of lube to fit my plug in. I made sure my ass swayed as I walked and as the first car pulled into the complex I stepped toward it, rather than hiding in the shadows.

"Looking for a good time?"

"Scarlett?"

"Craig?!"

I couldn't believe it. The first car I approached ended up being the man who left me empty and hungry.

"Scarlett, I was out looking for you last night and couldn't find you."

"I stayed in. Where have you been? I was out all weekend trying to find you."

"I was out of town. I had a prior trip scheduled."

"And you didn't tell me?"

"Did I have to?" Craig asked. "I thought you were a whore."

I laughed at the thought. He was right. And now here I was, leaning into his car window with my ass out for all to see.

"So what are you doing out here?" Craig asked.

"Trying to find a guy who wants to fuck me."

"Any guy? Not just me?"

"I am a whore."

He laughed at that.

"Five dollars?"

"Ten. A lady has standards."

"Get in."

I practically skipped around his car at the thought of swallowing his cum.

I had his dick out of his pants before he even got into the parking spot.

"Woah woah woah, slow down," he said. As he put the car in park I started sucking. "Geez. You're gonna suck my cock off! Ow. Scarlett. Ow!" he yelled as he pulled my head out of his lap. "What's gotten into you?"

"I'm hungry," I said, diving back into his lap. He caught my head and pushed me back off him.

"Slow down!"

I sat back into my chair, disappointed. I should be swallowing his load by now.

"I'm sorry. I just- I miss having your dick in my mouth."

Craig actually arched an eyebrow in surprise. "You miss my dick? I've never had a woman say that before."

"Well, it's true. I've been looking forward to having your cum in me for days now."

"Hey, hey, hey. Since when is this about you?" Craig held up a ten dollar bill. "You're the whore. I'm paying. This is supposed to be about me, remember?" I smiled at him. "Yeah."

"Go easy. Make love to it."

"Sorry."

"I want this to last," Craig said.

This time I kissed his cock first. Then I kissed it longer, like greeting a lover for the first time in a while. Craig sighed. I loved that sound. I slowly made love to his cock with my mouth and tongue. I could feel him getting harder, tenser, and after a very long ten minutes I knew he was about to explode. A second later he did.

I slurped up every drop before returning to my seat.

"So, same time tomorrow?" Craig asked as he started putting his dick away. I rubbed a bit of cum from the corner of my mouth before sucking on my finger.

"Definitely."

Craig handed me the ten which I promptly disappeared inside my bra.

"So were you with another guy last night?" Craig asked.

"What? No! Not exactly," I exclaimed.

"What's not exactly mean?"

"Well. It's hard to explain. Maybe I should just- show you?"

I looked down at the bulge in his pants. "You're going to need to take that back out," I said.

"You're going to suck me off again?" Craig asked as I started unzipping the lower zip on my suit.

"Not exactly," I said, smiling and wagging my eyebrows at him. I reached down and removed the butt plug with a soft "pop".

"Wait, are you-"

I cut Craig off. "Twenty bucks," I said.

He smiled at me. "I don't have any more money on me."

"Let's call this a freebie then."

"What do you want me to do?" Craig asked.

"Just put your seat back, down, and enjoy the ride," I said as I climbed on top of him.

I slid his cock into my ass as Craig moaned. I didn't have any lube but it still slid right in all the way up to his balls.

It felt incredible. The dildo felt good but this was something wholly different. My ass was alive with pleasure. I started bouncing up and down on top of him, riding his cock with wild abandon. Craig's moans turned into grunts as I started crying out in pleasure.

Craig grabbed my hips and started helping to pump my ass. He suddenly squeezed hard and pulled me as tight as he could onto his cock. I smiled down at him.

"How was I?" I asked.

"That was incredible," Craig responded. "Your ass feels so good."

My smile grew.

"Well in that case-" I started rubbing his crotch with my ass.

"What are you doing?"

"I want to go again."

"What did I tell you about what you want?"

"You haven't paid me yet," I said, continuing to grind into him. I didn't expect it but I could actually feel his dick growing inside me.

"I don't want to go again," he said.

"I do. My ass is still hungry for some of your delicious cum."

"I don't-" he started.

"Shhhhhh," I cut him off. "It feels like you do."

"I-"

I cut him off with a kiss. I thought I'd just put my mouth over his in a cute gesture to keep him from talking but before I knew it his tongue was inside my mouth, coiling around, over, and under my tongue. I kissed him passionately and felt something inside.

It's odd. I've had Craig's cock inside me multiple times now. Twice in my mouth, and he was building to his second orgasm in my ass but it was just sex. I was a whore after all. The act of kissing this man though, I felt... I felt my womanhood begin to swell inside me. I was Scarlett. I was a cock hungry whore. But I was also a woman with very feminine feelings.

Craig broke the kiss. "Wait."

I nibbled on his ear. I could feel him getting closer. In my head I was at war with myself. I desperately wanted Craig to cum inside me. At the same time, I didn't want this feeling to end and I knew once he came inside me it would be difficult (if not impossible) to get him to come inside me a fourth time. He gasped when came inside me for the third time that night. It felt amazing. It was better than I could have hoped for. Some women are lucky to get their man to cum twice a night. I just made Craig cum three times and I'd been a woman for a little under three months!

Craig shrunk out of me.

"Okay, okay. No more. I'm done for the night."

I climbed off him and slid my plug back into my ass. I wanted to savor Craig's cum inside me.

"That's forty dollars you owe me," I said, zipping myself up.

"Put it on my tab," he said.

I kissed him on the cheek before getting out of the car. I walked around to his driver side.

"I'll expect the money tomorrow night."

"What makes you think I'll be out here looking for you?"

"You will," I said before I started walking back to my apartment. I unzipped my suit so he could watch my ass as I walked away. I heard the car start up and he drove off but not before catcalling me out the window. He'd be back tomorrow.

My guts started hurting as I walked. I needed to fart. Badly. All that anal wasn't without consequence. I reached around and pulled the plug out. I let out a long fart and could feel cum begin to leak out my ass and down my leg. If I didn't zip up, I'd have a line of cum down my leg and along my boots.

It took half a second for me to get the idea to walk around the apartment complex again with Craig's gift leaking out of me. It made me feel like such a whore. It made me incredibly horny. I shoved the plug back inside me and started the vibrations. I almost missed Craig.

I noticed someone walking into a building and panicked. I was out here with cum on my leg, cum on my breath, my ass hanging out and filled with a plug. Then I saw Craig's car and realized who the figure was.

I kept to the shadows across the street and was able to see a light turn on as Craig entered his apartment. I knew where he lived!

I smiled to myself again. Tomorrow was going to be a great day!

That night I again slept on my couch, Craig on my breath and his cum on my leg. I'd worry about cleaning up in the morning. Besides, I loved the feeling.

The next evening I was dressed and ready to go out by ten o' clock. It was time to surprise my man. I wasn't sure if Craig would be turned on or upset that I knew where he lived. But I also realized that with more room we might be able to engage in other activities.

I left my apartment and made the short walk to Craig's. There was a light on and I could hear the television inside. I knocked on the door and then stood to the side so he wouldn't be able to see me in the peephole.

"Who is it?" I heard Craig from the inside.

"Delivery!" I said in my highest pitched voice.

"At ten o' clock?" I heard him ask but he still opened the door and I stepped inside.

"Hello," I said in what I hoped was a sultry voice.

Craig's face paled immediately. "What are you doing here?" he asked. "I mean, who are-"

"I thought tonight I'd let you fuck me from the comfort of your home."

And that's when I noticed Craig wasn't alone. There was another man sitting on his couch. Craig kept looking from the man to me and back again.

"This isn't- I have no idea who this person is," Craig stammered.

"Sorry, I should go," I replied, turning to the door and leaving.

"Wait," the man said. "Aren't you going to introduce me to your friend?"

I stopped in the doorway. The man took my arms and pulled me into the room as Craig closed the door behind me. "I'm Steven," he said.

"Scarlett," I replied.

"You're dating trannies now?" Steven asked Craig. Craig attempted to stammer a response.

"He's not dating me. I'm his whore."

"A whore?!" he exclaimed. "How much do you charge him?"

"I don't think-" Craig started.

"Ten dollars a blowjob. Twenty to fuck me in the ass."

Steven was impressed. "That's cheap."

"Well I don't do it for the money," I replied.

"What's in it for you then?" Steven asked. "Drugs?"

I laughed. "No. I love the feel and taste of his cum."

"I have plenty of cum for you," Steven said.

"Steven!" Craig exclaimed.

"It's okay," I said. "I don't mind."

"How about a two for one sale? Half price just for tonight," Steven asked.

"At the same time?"

"Twenty dollars, ass and mouth at the same time."

My heart started pounding again in my chest. I could feel myself growing excited. On principle I'd have to charge the twenty but an opportunity to be penetrated from both sides at the same time? I would have done it for free! I sauntered over to Steven and grabbed his crotch as I circled behind him. I stared right at Craig as I rubbed Steven through his pants.

"How about it? Want to play with us?" I asked.

Craig walked over to me, unzipping his pants as he did. I unzipped Steven and pulled out his dick. He was smaller than Craig but I didn't care. I was looking for quantity, not quality. I dropped to my knees but started bouncing up and down with my tongue out, giddy. I couldn't help it; I was super excited! I grabbed their cocks, one in each hand and gave them a tug. I started alternating between them, suck on Steven. Suck on Craig. Suck on Steven. Suck on Craig. I started sucking Craig and rubbing Steven's cock with my hand while the other hand reached beneath me and unzipped my catsuit. I pulled the plug out and dropped it on the ground with a plop.

I took Craig's cock out of my mouth and proceeded to jerk both men off from my knees.

"Yesterday Craig came three times inside me," I told Steven.

"What? No," was his reply. He looked impressed though.

"Think you can beat that?" I asked.

"Shut up and fuck me, whore," he replied.

I stood and took Craig over to the couch. I sat him down so I could suck him over the armrest. This left my ass up and exposed for Steven. He came up behind me as I was sucking Craig and slowly pushed his head against my asshole. He started squeezing it inside me.

"Come on. That's what the plug is for," I said around a mouth of cock and shoved my ass into Steven's crotch. His dick slammed into me, his balls slapping against mine. I moaned around Craig's dick. Steven slowly pulled out and slowly shoved back into me again. I'd never been so frustrated.

"I'm a whore. Fuck me like one!" Steven picked up the pace but I could tell he was going to need better instruction.

"Grab my waist and force me onto your cock!" I ordered. Steven finally got the idea. He grabbed me tight and started slamming into my asshole. I could feel his cock banging against my prostate and it felt amazing. I smiled up at Craig.

"Face fuck me like you hate me."

Craig smiled back, took my head in his hands and started abusing my face.

Finally! Two men were ravaging my holes. This is what I was made for. I could barely breathe with Craig's cock in my throat and Steven violently pounding my ass. I could feel them both building to a climax and I struggled to get Craig's dick out of my mouth. He fought back, pounding my face harder as I had asked.

When I finally managed to catch a breath I wasted it by asking, "please cum all over my face, sir." Craig seemed to love the idea. He shoved his cock back into my mouth and forcefully fucked my face. I heard Steven gasp and realized he was cumming inside my ass. A moment later Craig jerked my head off his cock and jizzed in my face. The warm, sticky ropes felt incredible. Steven pulled out of my ass, panting. He walked around me and dropped onto the couch.

"You're not done!" I pouted.

"That was amazing," Steven said but he didn't get off the couch. Instead he looked at me and laughed. "You've got something on your face."

I smiled at him. I licked my lips and tasted the cum that Craig deposited there. "Here. Twenty dollars." Steven handed me the cash.

"That's it?" I asked.

"Maybe tomorrow," Craig said. I reached out and took both flaccid cocks in my hand. I started rubbing and then kissed Craig's.

"Damn. You really are a whore," Steven said. "You don't quit."

"You haven't seen 'whore'," I replied. "How about this? I prove I'm the biggest whore ever, you two fuck me again. Tonight."

"How are you going to do that?" Steven asked.

"I'm going to walk around this complex. Just like this!" I answered, standing up.

"With Craig's cum on your face and my cum leaking out of your ass?"

"What can I say? I'm a whore! I'll be back soon and I expect two hard cocks." I left them alone in the room.

Outside I started walking around the apartment complex again. I did love the feeling of being exposed in such a slutty manner. I wondered if anyone would be able to tell I had cum on my face. And while my ass ached at the emptiness (I'd forgotten my plug inside) the feeling of cum between my ass cheeks was divine. I started to feel jealousy toward the real women. No matter how often Steven and Craig fucked me, I'd never be able to get pregnant. I'd just have to get used to being a cross dressing whore.

In no time I'd circled the complex and was back at Craig's building. I heard Craig's laugh and looked up the stairs to see Craig and Steven both standing outside his apartment door.

"Hey boys!" I called up.

"I told you she'd do it," Craig said. "Fifty bucks!" Steven muttered something and disappeared back inside.

"You just made me- us, fifty dollars," Craig said.

"Oh yeah?" I asked. "I missed you."

Craig smiled down at me.

"Is it okay for me to tell you I missed your dick, too?" I asked.

I don't know what compelled me to do it but I dropped down on all fours and started crawling up the two flights of stairs to Craig's floor. When I arrived, Craig opened the door and I crawled inside.

Steven was sitting on the couch, watching TV but he turned when I crawled into the apartment.

"You're crawling now?" he asked.

"I'd crawl miles for a chance to suck your cock," I replied.

"You really are a whore," was his answer.

"Leave her alone," Craig said as he closed the door. "You're just upset I won the bet."

"Whatever," Steven said and turned his attention back to the TV. I crawled across the floor to him and pouted.

"Does this mean you aren't going to let me suck your cock?" I asked.

Steven just stared at me. I smiled at him but he didn't react. Finally I unzipped his pants and pulled out his stiffening dick. I ran my tongue along the whole shaft, keeping eye contact with Steven the entire time.

"You might be mad at me but your cock still likes me," I said.

I noticed Craig was behind me now so I stood up, giving him access to my ass.

"Do you ever get tired of cock?" Steven asked.

My smile got wider. "Nope. I'm a bad girl."

"You are a bad girl!" Craig said. I shook my ass at him.

"This bad girl needs to be spanked."

Craig smacked my ass with his hand. I moaned into Steven. "Mmmmmm. I need more." Craig smacked my ass again. "Harder," I mumbled around Steven's cock. Craig hit me even harder. "Spank me harder, Daddy?" I begged. Craig started smacking my ass, alternating between cheeks. My ass was going to be red in the morning. "Oh, yes," I cried in Steven's lap. Craig continued his assault on my cheeks for several minutes before he plunged his cock into my ass. The combination of the soreness of my cheeks and the fullness of my ass was driving me wild. I sucked Steven's cock harder, deep throating it and curling my tongue around his shaft.

Craig would thrust his cock into my ass, pull all the way out, slap my ass cheeks, then plunge all the way back in again. Over and over.

Steven's cock was hard but he was still watching television with a disinterested look on his face. I pouted again as Craig continued his assault on my rear.

"What's the matter?"

Again he looked at me with disdain.

"You're getting fucked in the ass and you're so loose you don't even notice anymore."

I smiled at him. "Maybe if you both fucked me in the ass at the same time?"

"And then when your ass got loose enough? What then? Three guys? Four guys? Ten? How many's enough for you?"

Mmmmmmm. I'm sure I licked my lips thinking about it. Why not ten guys? Or twenty? Could I find a hundred men willing to fuck me at the same time? I imagined all that cum running over my body; bathing in it. Would that be enough?

I thought about what I was doing, down here between Steven's legs as Craig thrust into my gaping hole. A few months ago, dressing up as a woman was only a fantasy of mine. Last week I was going out of my mind, craving Craig's cum in my throat. Now here I was taking two men at the same time. Where would it end? Would a hundred cum shots be enough?

Of course it wouldn't! If I could fuck every man in this city, every man in this state, I would. I love cum. I'm an addict. I love the smell, the taste, the texture, the way it looks! I love cock. I love it in my hands, in my mouth, and in my ass. I am a whore. I'm more than a whore. I'd do it for free! Steven was right. I'd never have enough. My only regret was I didn't have a pussy to be fucked in at the same time.

As I was daydreaming Craig finished in my ass and went to the kitchen. I slid up into Steven's lap and sat on him, his cock in my ass. I wrapped my arms around him and looked deeply into his eyes.

"Hey, so I'm a slut. Don't I turn you on?"

I ground my ass into his legs. I knew I could make him hard.

"Yeah. Just, I don't know. I've never had sex with a guy before."

"Is that all?" I grabbed his hands and put them on my body. I slid them across the slippery PVC, along my waist and up to my chest. "Does this feel like a guy's body to you?"