Becoming a Whore

Anal

I wasn’t a very popular teenager. I had no friends and spent a lot of time by myself. I didn’t even have a girlfriend until I was in my early twenties. So I spent a lot of time watching porn on the computer and jerking off. At first I was watching vanilla porn. I’d watch women eating each other out and watch men fuck attractive women and imagine what it must be like to have a girlfriend.

Eventually though, things started to change. I realized the difference between the men in those videos and myself was the fact that women wanted to have sex with the men in those videos. They chose. They had the power. I started thinking about what it would be like to be the woman.

It wasn’t something I acted on, just a fantasy, a switching of positions I imagined myself in. I was watching a lot of lesbian porn at the time so I was still fantasizing about having sex with a woman, I was just wearing sexier clothes while doing it. I imagined I was driving people wild with lust as they watched me and my girlfriend.

Eventually I started dating and all the fantasies (as well as the porn watching) disappeared. I was incredibly happy with my girlfriend. We quickly got engaged. We were going to be together forever. It was finally happening to me!

And then she broke up with me. I was devastated. I didn’t want to do anything but lie around my apartment and be miserable. I relocated out of the state and decided to try and start a new life elsewhere.

I found myself a new job and a new apartment. I didn’t have any friends but I was used to that by this time. I’d go to work, go to the grocery store, come home, eat dinner and go to bed. I spent my weekends watching television.

Eventually I “rediscovered” porn. I started watching with a vengeance. I was yanking on my cock four or five times a day. I’d masturbate in the morning, at work in the bathroom, on my lunch break, when I got home, and before bed. It didn’t take long before I began imagining myself as the woman again. I started to think about purchasing some women’s clothing to wear. Then I thought “why stop there?”

I had a bit of money (I wasn’t spending it on anything but food and rent) so I settled on purchasing a PVC catsuit, 6″ thigh high boots, a set of breast forms, and a vibrating butt plug. I didn’t want something I was going to use for a week and discard so I bought an intermediate size. My heart was pounding in my chest as I pressed the “purchase” button. Was I really doing this?

I jerked off and went to bed.

The next three days were like a dream. I actually didn’t masturbate at all. Had I really bought a sex toy? Was I really planning on wearing women’s clothing? The third day I arrived home to find a large box waiting for me. I brought it inside, closed all the blinds on the windows, and cut the box open.

It was like a depraved Christmas. On top was the catsuit in a large box. The model on the cover was so sexy. Would I look like that? The boots were scary. I had no idea how I would ever walk in them. Next up was the butt plug. It looked HUGE in my hand. How would I ever fit this massive thing inside me? Lastly were the breast forms. They felt real. I held them up against my chest while looking at myself in the mirror. No time like the present I guess!

I put the forms in the bra they came with and struggled to clasp the bra behind me. My back immediately felt the new weight on my chest. I slid into the catsuit, zipping it all the way up to my neck. It felt so tight on my body as if it were hugging every inch of me. I sat down on my bed and unzipped the boots. I put my right foot inside and zipped it up. It fit! I tried on the other one and then stood.

The first thing I noticed was how much taller I was. The second was how difficult it was going to be to walk around in these! For the next five minutes I staggered around my apartment like a drunk, catching myself on the walls and furniture as I almost fell. After that they started hurting my feet and I had to remove them. I peeled myself out of the catsuit and sat on the side of the bed, eyes on the plug.

I entered the bathroom and lubed up the plug. I reasoned it would probably fit in easier if I was squatting over the ground. I started pushing the plug into my virgin asshole. It felt weird at first but quickly became painful. I grimaced in pain before pulling it out again. I examined the lube on the plug and realized I’d fit maybe a third of it into my ass. There was no way I was going to fit the whole thing. Disappointed I returned to my bedroom, turned on my laptop and went to my favorite porn site.

I performed a search for anal and found a video of a woman playing with a butt plug. It was a small one, smaller than the one I owned. She slid it into and out of her asshole. I was jealous. She put the plug aside, however, and then brought out a plug about the size of the one I owned. “Now I’m going to try and fit this one for you,” she said as she smiled at the camera.

Excited, I brought my laptop with me to the bathroom and decided that if she could make hers fit, I’d make mine fit. Together, we worked on yalova escort shoving our plugs into our asses. We’d push for a few moments, then add more lube, then try again. Her’s popped into her asshole at the same time I gave a final, painful shove, feeling as if my asshole was going to tear, just before mine popped inside too! I was so proud of us. I felt like we’d both achieved something incredible, separated by a computer screen. As the pain dulled to a sore asshole I started feeling something amazing. I felt so… full. It felt like nothing I’d ever experienced. I hurried back to my bedroom and put the catsuit and boots back on.

My feet and asshole were still sore but I didn’t care. The full feeling in my ass combined with the feeling of the tight PVC and the heavy weight on my chest left me in heaven. When I turned on the vibration, well…

As the days went by it became easier and easier to fit the plug in my ass. Eventually the pain went entirely away. It was rare to have an hour at home when I wasn’t plugged or wearing women’s clothing. I spent my nights and weekends, plugged, dressed, and in pure bliss. I added makeup to my repertoire and began shaving off all my body hair.

After a couple months I started wondering if I dared go out in public dressed this way. I’d started doing my shopping in panties; I didn’t own a single pair of male underwear anymore. My socks had been traded for thigh highs and panty hose two weeks after my first purchase. I was playing with myself more than ever before and I started watching dirtier and dirtier porn. I decided that night I’d try going out in only women’s clothing while wearing my plug.

It was dark and I thought the chances of myself being caught were fairly slim. It was around 130 in the morning on what would then be Friday. I don’t know why I was so excited to try this. I suppose it had something to do with the chance of being caught, being discovered. My femininity no longer being a secret between myself and the locked bag under my bed but sharing it with someone else. I dressed in my catsuit and boots, I had my plug in, lavender lipstick, I put on a long trenchcoat, took a deep breath and stepped outside.

In my nervousness I forgot to lock the door to my apartment. I started down the stairs which a few months ago would have been impossible in my 6″ heels but I’d had a lot of practice since then. Emerging from my building I looked around. There were a few lights on here and there in the complex but it was quiet. There was a major road nearby and I could hear cars on it even at this hour but my complex was empty. Not a single late night dog walker or person coming home from a club. I smiled to myself and started walking.

I’d decided to do a circuit of my apartment complex. It shouldn’t take longer than ten or fifteen minutes. I strutted my stuff as I walked along the road, the sound of my heels loud in my ears. I grinned to myself. I was having fun. The vibrator purred nicely in my ass, swaying with my walk. I opened my trench coat and let my breasts out. In my head I imagined I was a street walker. Maybe I was on my way to some late night client’s house to give him a quickie. This was fun!

My apartment was near the back of the complex so about five minutes later I found myself approaching the front gate. I was so lost in my fantasy I didn’t even notice the car pulling into the complex. I heard a whistle.

“Hey! What are you doing out here so late?”

I panicked. There was another resident, here, pulling up next to me. I looked the other way, praying he’d just drive away.

“Hey, are you okay?” the driver asked, now sounding concerned. “Do you live here?” How could I have possibly been so stupid? “Are you locked out of your apartment? That’s an odd outfit to be locked out in?”

It was obvious he was not going to just drive off. I stopped walking, took a deep sigh and turned to the car.

“I’m just out for a walk, thanks.” There was no way he could possibly mistake me for a woman. And I lived in the same apartment as this guy!

“Oh. Sorry. Um. Nice clothes.”

“Thanks,” I replied.

“So, uh, do you need a ride?”

Are you kidding me? This guy was going to give a cross-dressing street-walker a ride to his apartment?

“I, uh. I’m just up here,” I stammered.

“Same direction I’m going.”

At that moment another car started pulling into my complex. That decided things for me. I didn’t want two of my neighbors to discover my fetish. I got into the car.

He held out his hand to me. “I’m Craig.” “Hey, I’m-” I hesitated. “Scarlett.” “Nice to meet you, Scarlett,” he said with a smile. He kept staring at me and I didn’t know how to react to that. “I’m just up ahead.”

“Oh, right.” He put the car in gear and drove up to my building. He pulled into the spot and put the car in park before turning to me with that same odd stare. “Uh, thanks,” I said and reached for the door handle.

“Does that stuff feel good?” Craig asked.

“What stuff?”

“The outfit? The makeup? Do you like looking like a girl?”

“I zonguldak escort guess so,” I replied.

“Do you, uh, do other stuff?”

I hesitated. “What kind of other stuff?”

“Other, you know, girl stuff. Do you sit when you pee?”

I actually had started sitting down every time I peed. It felt more natural to me. “Yes.”

“Do you always wear girl clothes?”

“When I’m at home. When I’m at work I wear stuff under my work clothes.”

“Do you ever think about… guys?”

Oh, so this is where he’s going. I thought about the girls I saw in those pornographic videos. They always looked so happy in the arms of a powerful man. Craig wasn’t overly muscular but he wasn’t out of shape.

“Sometimes,” I said. What the hell? I gave him what I hoped was an inviting smile. “What did you have in mind?”

“Have you ever been with a man?”

“No. Not yet anyway.”

“But you’d like to?”

“I am dressed in a sexy outfit. I was out walking the street.” I was so awkward back then!

“So you’re a prostitute?”

“I prefer the term ‘whore’.”

“So how much?” he asked.

“How much what?” I asked, confused.

“How much do you charge for a blowjob?”

“Oh, ummm, ten dollars,” I replied, saying the first number that came to me.

“That’s pretty cheap,” he said.

“So am I!” I replied, getting excited. I really was so awkward.

“Well, let’s go in,” he said and reached for the door handle.

“No. Wait.” I reached out and took his arm. “Let’s do it in here.”

“In the car?”

“It’s dirtier that way.” I pointed behind us to a parking spot that wasn’t illuminated by a street light. “We could go right over there.”

Craig thought about it for a moment. “Please,” I begged, “I want my first one to be special.”

He started the car, backed out of the space and reparked in the dark spot. He turned the car off, slid his seat back and put his arms behind his head.

“You’re up.”

I had no idea where to begin. I thought he’d just pull his dick out and shove it in my face. This was not what I expected. Craig noticed my hesitation.

“You’re the pros- I’m sorry, whore. So you’d better take my cock out and begin or I’m not going to pay you.”

I leaned out of my seat and unzipped his pants. I could feel the large bulge under his jeans and as I slid my hand into his pants I felt it get bigger. I struggled to find the hole in his boxers but as his cock got larger the space inside his pants was becoming tighter and tighter.

“You’re gonna have to take my belt off and undo my pants,” he said. “You’re not very good at this. I’m going to expect a discount.” I apologized and started undoing his belt. A discount? I was about to put his cock in my mouth and swallow his cum for only ten dollars and he wanted a discount? I opened his pants and a large cock flopped out, quickly becoming erect. He was bigger than I was; at least 6, maybe 6 and a half inches. At the time it looked huge to me! I started having doubts. Was I going to be able to fit this whole thing in my mouth?

“Start sucking,” Craig said.

I leaned down over his cock and licked the head. It tasted… good. Salty. Kind of like sweat but different. It had a texture unlike anything I’d ever wrapped my tongue around too. It was firm yet somehow, soft.

I ran my tongue around his head over and over and over again, getting used to the sensation. I took his cock in my hand and licked the shaft from the balls to the head. I did it again, next to my previous trail of saliva. And again. I went as far as I could around his dick, licking it until I returned back to the start and ran my tongue around his head again.

I started planting tiny kisses around his head.

“I thought you were a whore, not my girlfriend,” Craig said as he grabbed the back of my head and shoved my mouth entirely around his cock.

I felt his dick slam into the back of my throat. I gagged and tried to pull my head off his dick but he held me there, impaled on his cock. I couldn’t breathe. I felt like I struggled against Craig for ten minutes but in hindsight it was probably more like ten seconds before he let me go.

I came up coughing, tears streaming down my face and fell back into my seat.

“I’m sorry. I don’t know what came over me,” Craig stammered. “I was getting into the roleplay and-“

“It’s okay,” I gasped, still struggling to catch my breath.

“I’m. Here,” Craig said, holding out fifteen dollars. “It’s all I have on me right now.”

“The deal was for ten.”

“I’d rather you just take it all. I’m sorry.”

“Well, okay,” I responded, reaching out to take his money. I reached for my wallet but realized I didn’t have pockets in my catsuit. I unzipped the suit and slid the money into my bra.

“Now I really have to fulfill my end of the bargain.”

“But-“

“I still want to swallow your cum.”

I zipped up again and gleefully slid my mouth back down over his cock. I hungered for his sperm inside my belly in a way I’d never hungered zonguldak escort for anything before. All I could think about was getting his thick, creamy, salty load to slide down my throat. I sucked him with my lips, licked him with my tongue, and massaged him with my throat.

After a minute I looked up at Craig and saw him staring at me in surprise and confusion. It was obvious he’d never been with a woman as ravenous as I was.

“Well?” I said with a much better smile. “Grab my head and treat me like your whore. It’s what you paid for.” I took his hands, placed them on the back of my head and slurped down his cock like the girls in my porn. After a moment he twisted his hands into my hair and shoved me back down onto his cock.

Five minutes later I was sweaty, tears running down my face, gasping for air, chin soaked in saliva and ball sweat, and a mouth full of delicious, salty cum. I smiled at him, swallowed, and said, “Thank you. That was delicious. I should be paying you.”

“Keep it,” he sighed, still leaning back in his chair, “you definitely earned it.”

“See you tomorrow?” I asked.

“Ten dollars?”

“Make it five.” I got out of his car and walked up to my apartment.

I woke up the next day, stretched out on the couch, feet sore from falling asleep with my boots still on. My mouth tasted funny before I remembered the last thing I’d had in there was Craig’s cum. The thought of sucking his cock again tonight made me horny again. I reached for my plug’s remote and tried to turn it on but the batteries had died sometime last night and besides, I had to get to work. I got off the couch and showered. I put my usual panties on and then had a dilemma. My plug needed to be recharged but I was feeling especially feminine that day and wanted to leave it inside me all day. Heck, maybe I’d only take it out from now on to go to the bathroom. I was going to need another plug. I ordered it before leaving for work.

I felt amazing all day, constantly thinking about Craig’s cum in my belly. It wasn’t even that I wanted more, I needed more. I ached to feel his big dick in my mouth. My tongue wanted to be swirling around his cock. Time passed agonizingly slowly.

When I arrived back home things weren’t much better. I still had hours before I could walk out on the street and hopefully find Craig again. I realized I didn’t know where he lived and it was a good thing because if I did know I would have been outside his door, begging for him to open up, throw me to the ground and force feed me his cum. What was happening to me? There were only 800 or so apartments in my complex. Maybe I could go door to door. What if he wasn’t home? Maybe another man would take me into his apartment and satisfy my need. I was going crazy. Why wasn’t my butt plug here yet? I signed onto the internet and went back to the toy store. I ordered myself an 8 inch suction cup dildo. If Craig wasn’t going to be available 24/7 for me to suck I’d have to find a replacement.

It couldn’t have been later than 12:45 before I left my apartment and took up my position on the street, frantically searching for Craig’s car. Every time I would see a vehicle I’d become giddy, then, when the vehicle turned out to be driven by someone else I’d retreat into the shadows until they passed.

I was out until 3 in the morning before I returned to my apartment, dejected and hollow. Where was my cum? Was Craig mad at me?

I spent Saturday and Sunday night walking the streets again. A few times I debated stopping a car and finding someone new. The complex was in the suburbs of a major city and a few times I thought about driving into the city and walking the streets there. I needed a man to satisfy my cum cravings. I was going insane.

Monday night I stayed in. Tuesday when I arrived home I discovered another package. I rushed inside and tore it open, ripping a hole right through the side of the box. Within were my new plug and new dildo. It was bigger than Craig and bright pink. I mounted it on my shower wall and remotely activated my plug. I went to work sucking the dildo.

It didn’t taste as good as Craig did and the feel was off. But it was large enough to give my jaw that aching feeling. After a half hour though it was obvious this was not going to be enough. No matter what I did, this dildo could never fill my throat with that tasty cum. That’s when another thought came to me.

I moved the dildo lower on the shower wall. I then unzipped my catsuit’s lower zip and removed my plug. While big, the plug wasn’t as large as the dildo. A few months ago there was no way I could shove this thing into my ass without tearing it but now? I lubed the dildo up and moved my asshole so the tip was just against me.

I started pushing back, slowly at first before deciding, “The hell with it. Am I a whore or not?” and impaled myself on it.

I was in agony. I cried out in pain and then knelt there, dildo buried to the silicon balls in my ass. If I moved I was sure to be in pain. I slid forward a bit and bit down on my lip as my ass protested. With agonizing slowness I removed myself almost entirely from the dildo. When just the tip was left in my ass I stopped. A moment later I started sliding it back in. I don’t know why, I just wanted the dildo back in my asshole. When my cheeks hit the balls I pulled back out again.

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