Ladies Night

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A young man is transformed into a young woman.
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SRound
SRound
130 Followers

(All characters are 18 or older.)

.............................................................................................

"Fuck me hard with that huge black dick!"

I sat on the couch and turned up the volume on the TV, trying to drown out the sounds of sex coming from my sister's bedroom. She had her "boyfriend" Russell over again. Russell was tall, black, and supposedly very rich. Whenever he came over they always went right to her bedroom and never came out. He wasn't really her boyfriend. They never went on dates or did anything romantic. My older sister Jessica was simply his booty call. And lately he had called a lot. He did something important for some big local business according to her. Whatever it was, he had a lot of money and a lot of free time. One of his favorite pastimes apparently was collecting college girls. He met my sister one night at a bar and liked what he saw. All he had to do was flash some cash and buy her some drinks and she let him do whatever he liked. He must have liked loud sex.

"Who owns this pussy!? Say it!"

"You do! It's yours. It's your pussy baby." My sister's bed was creaking loudly, further painting the picture in my mind of just what was going on behind that door.

"Damn right," he said. It was followed by a loud slapping sound.

Jesus, I could even hear the smacks on her ass. I guess that is what happens when you live in a tiny house meant for college students. It was affordable and it had two bedrooms, but there really was next to no privacy. Maybe if it wasn't my sister I had to listen to I wouldn't have minded so much.

"Oh my God! Oh my God!" she cried as their fucking apparently ramped up in intensity.

I tried to pretend that she was only praying. I didn't know what to make of the grunts I heard mixed in with it though. I would have just left to do something somewhere else, but I didn't have any money to waste. I had plans later to watch a movie with some friends, and I barely had enough to do that. It was also incredibly cold outside, so I wanted to stay indoors.

"You're such a fucking slut. You love getting fucked don't you?" he said.

"I do, I love it. Use me, make me your dirty whore." She was out of breath, and it sounded like she was barely able to get her words out. It was clear from the sound of her voice that she was enjoying herself though. He had her in the palm of his hand. It made me sick.

"Get down, I want to cum on your whore face."

"Yes baby, cum for me!" my sister cried.

"Ahh, Fuck!" A deep moan was mixed together with an appreciative cooing sound coming from my sister.

Well, at least they were finished. They had been at it for the better part of an hour. At first they would try to be a little discrete, but they always got loud in the end. It was hard to hear that for many reasons. I wasn't a prude and I didn't mind that she was sexually active, but I wished I didn't have to hear it all the time. Any time I tried to talk to her about it she just dismissed it as her little brother being annoying and told me to mind my own business.

Eventually the door to her bedroom opened up and Russell came out. He was buttoning up his expensive looking dress shirt. Seeing me on the couch with the TV volume turned up super loud, he gave me a cocky smile and winked. What a tool. He made his exit without saying anything. He had driven over in a brand new Cadillac. It looked cool and was just the kind of car I wished I had. I didn't doubt that he was loaded, but nobody I talked to seemed to have any idea just how much he was actually worth. Just having a good job at some small business wouldn't be enough to afford the brand new cars I had seen him drive. It was a personal goal of mine to find out exactly where his money came from and how much of it there was. I heard him start up his car and drive away. A few minutes passed before Jessica came out of her room and joined me on the couch.

"I can't believe you let him treat you like that," I said.

"I can't believe you listen to us all the time. You're such a perv Sam."

"Oh, like there is anywhere in the house I can go to not hear you. Why don't you just go to his place?"

"He likes doing it here," she said. "You're just upset because you aren't getting any yourself."

"Well it isn't as easy for me. I have to work harder than just spreading my legs like you do to get sex. Women have it easy."

She laughed. "I get more than just sex for spreading my legs." Reaching into her pocket, she pulled out a wad of cash and flashed it to me. It was a mix of twenties and hundreds. There had to be close to a thousand dollars there!

"Holy shit!" I said. I couldn't believe it. I worked my ass off at my part time job for minimum wage and I barely had enough for a movie after paying for school expenses. She let a man have his way with her for an hour and she gets a thousand dollars!? It's not like she didn't enjoy the sex either.

She smiled at my shocked expression. "Yep, he likes taking care of me. All I had to do was drop a few hints about wanting some new clothes and he gave me this."

"You know he probably has a wife he is hiding from you," I said trying to find something to wipe the smug smile off her face.

"Probably. He has a lot of other girls from the college that he sees too. Who cares? As long as he takes care of me like this, he can do whatever he wants," she said.

My sister was basically a prostitute. She had a sugar daddy that used her for sex and paid her handsomely for it. And I was jealous. Why couldn't something like this happen to me? Attractive women like my sister could live in luxury on their looks alone. It wasn't fair. My mom was the same way. She was a manipulative woman who left my Dad when he lost his job and jumped to someone new who could afford to buy her fancy things. That was when I learned that love wasn't real. It always drove me crazy to see the men she was with buying her whatever she wanted when she gave them nothing in return. My sister must have seen that as a lifestyle to aspire to.

"So I'll be heading out to the city tonight with a couple friends. We are going to stay the weekend and do some major shopping. I'll be back before Monday sometime, so try not to burn down the house."

I barely managed to grunt in acknowledgement of what she said. I was too consumed with envy to think rationally. If I had money like that, things would be so much easier. I wouldn't be spending it on dumb clothes either. Could there be any rich women around looking for a boy toy? Of course not. My slutty sister had all the luck.

A little while later Jessica said goodbye and she was off to spend her new stack of cash. I spent another hour watching TV and stewed over how all the women in my life got everything handed to them. Eventually it got close to movie time, so I showered and got ready to go out and meet my friends. We were meeting at a fast food restaurant for burgers and then seeing the movie after. It sounded like just the right thing to cheer me up.

.............................................................................................

Tom and Derek were two of my best friends at school. The three of us were computer science majors, and we shared most of our classes. The burgers we had hit the spot, and the movie was a lot of fun too. It was the most recent super hero movie to hit the big screen. We were suckers for any comic book film, and we had been looking forward to seeing this one for a while. It was close to ten when the movie finished. We began going over our favorite parts while we headed to the parking lot.

Tom stopped just before we reached our cars. "The night is still young boys. What do you say about having some fun across the street?"

The parking lot for the theater happened to be right next to The Pit, a local club and popular party spot for the town's college kids. There was beer, loud music, and lots of pretty young girls dancing and flaunting their stuff. It would definitely make for a fun night. My problem was that I couldn't afford it.

"Well I'm in the middle of a long dry spell right now, so I'm game. I haven't scored since that night with both of your mothers," Derek said. That earned him a couple punches.

"I don't know guys, can't we just go play some xbox or something? I don't really have the money for partying tonight." I said.

"Oh come on, just come hang out with us at least. I'm sure some fugly girl in there would love to buy you a drink," Tom said, laughing at his own joke.

"I really can't tonight."

Tom and Derek turned to look at each other. Coming to a silent agreement, they nodded in unison. "Sucks to be you. We'll let you know how the night went. See you on Monday, man." Tom said. With that, they headed across the street. What jerks. I watched them get to the doors just behind a group of girls who looked dressed to kill. The man at the door waved the women in before charging my friends the entrance fee. It was then that I noticed the big sign hung by the door that said "Ladies Night! Free admission for any lady with a college ID!"

My mouth dropped. I couldn't believe it! Again I was witnessing women getting what I couldn't have based on nothing more than their gender and good looks. Just by being a young lady in college you could party and get drunk completely for free. I, however, was going to have to spend the night in my shitty house playing video games alone and sober. It was more than I could take. Normally I would have simply laughed and shook my head upon seeing women get into a club for free. It isn't really anything new. But after what happened with my sister earlier in the day, something inside me snapped. Deep down I knew I was angrier at my own situation, but I began to heatedly rant against women. I shouted about the injustice of it all. All my frustration from the day poured out of me as I railed against the manipulative and using nature of all women everywhere. Eventually I stopped and quieted down. I actually felt relieved to have let off some steam like that. I began to get worried that someone might have heard me, so I quickly looked around to see if I had caught anyone's attention. I sighed in relief seeing that nobody was in the area. Making my way to my car, I prepared to head home. That was when I heard the laugh. I turned to look at the source and saw an old lady that was standing in an alley between two buildings at the back of the parking lot. She was looking right at me and obviously laughing at my outburst.

"You are funny boy," she said. She had long gray hair covered by a purplish bandana. Her clothes were old and dirty. A blanket was wrapped around her body and she was standing next to a garbage can containing a fire. I don't know how I missed her before. Guilt flooded me when I thought maybe I had just subconsciously ignored her because she appeared to be homeless. The guilt was replaced by embarrassment when I remembered what she must have heard me say.

"I do not think you are liking women much," she said.

She had a funny way of talking. She didn't seem to be angry at all, though. I really wanted to drive away and leave the whole scene behind me, but I didn't want to be rude. I decided the least I could do was apologize to her.

"I'm sorry, I didn't really mean all that stuff I said. It... it has just been a rough day."

"What could have happened to make you say such things, I wonder?" she said.

"It's just... well between my sister making more money from one night of sex than I do in a month and seeing those girls get into the club for free, I kinda felt like it was all unfair you know?"

"I see. That does sound troubling."

"Anyways, I'm sorry again for what I said. I'm heading home now." With that I turned to my car, intending to finally head home.

"Wait, boy. I think I can help you with your problem."

I stopped. Help me with my problem? What could she possibly do to help? I should have just ignored her and got in my car, but I didn't. She was being nice to me despite the rude things I said, so I reasoned I should at least hear her out. Whatever piece of wisdom she planned to impart upon me might even be worth hearing. I walked to where she was huddled close to her fire.

"Hold out your hand, boy," she said.

I was only expecting her to give me a bit of clever advice. Not knowing what she had in mind, I hesitated. However, curiosity got the better of me and I slowly extended my hand towards her like she wanted. Faster than I would have believed possible for someone her age, she reached out and firmly grasped my hand.

"Hey! What do you think you—Ahhhh!"

A green light shot up my arm from where she had a hold of my hand and I screamed in surprise. It felt like some peculiar energy was sent into my body. I tried to pull my hand away as soon as she had grabbed it, but her grip was abnormally strong. She continued to keep a tight hold of me despite my struggling. Soon my whole body began to glow with that same green light that I had seen fly up my arm before. After a few more seconds, she finally released me. I stumbled backwards into the wall of the alley.

"What did you do to me!?" I shouted at her.

She did nothing but smile and watch. Fear filled me as I stared at my hand that was glowing with the eerie green light that now covered my whole body. As I watched it with wide eyes, my hand began to change. My hand seemed to shrink and my fingers became thinner. I could also feel the change happening along with seeing it. It was an odd sensation. There was no pain, but I could clearly feel my skin and bones shifting and moving into new positions. Only a moment later I could feel the same shifting happening everywhere else in my body. The hair on both my arms was sucked into my skin which seemed to be becoming smoother. My clothes became slightly baggy as if I had shrunk down in size. The change that grabbed my attention the most was with my penis. It felt very similar to getting an erection, but instead of feeling my member pulsing to full strength, with each pulse it shrunk and was pulled within me. Feeling my penis disappear shook me out of my stunned silence.

"Wha... what is happening!?" I said. She remained silent. I probably wouldn't have heard her if she had said anything because I was shocked at the sound of my voice. As I spoke, my voice changed from normal to a much higher pitch. Hair blocked my vision as it grew out at an astonishingly fast rate. Feeling a large rumble throughout my body, I saw my chest begin to expand. My shirt was pushed out as two breasts of impressive size filled out on my now more slender form. With that the green light faded and my body was still. I quickly surveyed my body to check the damage she had done. It became very clear what had happened after a few moments. I was now a woman.

I was shaking at what I had just witnessed. I couldn't explain it, but I knew that I had been transformed somehow. The old lady was still standing there with a smile on her face. "How?" I asked. "Why?" I had to remind myself that the young girl's voice I heard talk just then had actually been my own.

"I give you gift, boy," she said. "You think women have easier life than you. Now you can live just as they do and find out for yourself if true."

I stood up and angrily said, "I don't want to be a girl! Change me back!"

She laughed. "No. This is great opportunity for you. Embrace it and live as woman now."

"You mean you are just going to leave me stuck like this?" A sick feeling came over me. Was this really happening? Feeling faint, I collapsed against the wall and put my head in my hands.

"The change will not last forever. Is only for one day. Tomorrow night, you go back to normal."

Thank God. I would be able to hide at home and nobody would ever know. Relief poured over me. For the first time since she grabbed me I started to feel close to calm. I stared at my new feminine hands, half expecting them to go back to normal any second.

"But beware," she warned. "If you take the seed of a man into your womb, there is no going back. You will be woman forever."

"There is no way I'm having sex with a man," I told her.

"More than just body has changed. The mind changes slower, but soon you will even think like woman."

I didn't like the sound of that. What did that mean? On the outside I was definitely different, but inside I felt the same as before. I doubted that whatever change she mentioned would affect me too much. Maybe I'd start to crave a ton of chocolate. I suddenly realized that while I had been thinking, the old lady had begun to walk down the alley.

"Hey, wait! I'm not done talking about this." I shouted. I got up and hurried after her. I stumbled more than once. My body was unfamiliar and my shoes were slipping with every step. The old woman turned a corner when she reached the end of the alley. I was only a couple seconds behind her, but when I turned the corner, she was gone. It was as if she had disappeared. It reminded me of a scene out of some cheesy movie. If I hadn't already witnessed my own body transforming like I did, I wouldn't have believed that someone could just vanish like that. But now I knew that magic actually existed in the world. Anything seemed possible.

.............................................................................................

I made my way back to the parking lot and at long last got into my car. I was thankful now that my sister was away shopping. How could I possibly explain this to anyone? Nobody would believe me. Luckily it was the weekend so I didn't have to go to class. The drive home was uneventful besides the endless questions that bombarded my mind. When I arrived at the house, I went directly to my room and took note of all the changes that had occurred in my body.

I took off my clothes and stood naked in front of the full length mirror in my room. It was very shocking to see a new person looking back at me. Where I used to have straight lines, I now had sensual curves. The small belly I had was gone, the fat having been moved to form two large perky breasts. My pubic hair had diminished and all that remained was a small triangle of dark hair above where my penis used to be. A small pink vagina was between my legs. I slowly spread it open with my fingers to get a good look at it. It was exactly the type of pussy I loved to see on women.

"Damn... I'm hot," I said to myself. I was a raven haired beauty. My hair was slightly wavy and reached halfway down my back. I flipped my hair over my shoulder and turned around to see my backside. "A nice ass too." It was big, but not absurdly so. It looked perfect for the rest of my body. I had some fun watching it jiggle as I gave my hips a shake.

Maybe I was looking at this situation all wrong. Sure, I wasn't happy about being transformed against my will, but it was only for one day. I had the house to myself and a female body to play with. What more could a guy ask for? I grinned as the new possibilities came to me. I sat on the edge of my bed facing the mirror and spread my legs wide.

My new pussy had small labia and looked like a smooth pink slit. I noticed while admiring it in the mirror that it was beginning to get wet. The naughty thoughts that I had started thinking must have gotten the juices flowing. I ran a finger slowly along the edge of my pussy lips before pushing two fingers inside. It was tight and squeezed hard against my fingers. I slowly pushed the fingers all the way in and out and then repeated the motion. It felt good. It was different from stroking my dick, but it was still enjoyable. Somehow having my pussy stretched and filled felt very satisfying, as if I had found something I was missing. I watched myself get fingered in the mirror. The wetness of my pussy kept increasing. I brought out my fingers that were covered in my own lubricant and tasted myself. It tasted sweet and I couldn't help but moan from the naughtiness of it all.

SRound
SRound
130 Followers