Natalies Business

By Marcia Fredricks

Published on Jan 1, 2005

Transgender

It had been an exhilarating night. Home in Natalie's apartment, I stumbled into bed and fell into a stopper-like sleep. My dreams were unsettling. They were exciting but they also repulsed me and when I woke, I lay in bed pondering their validity. I wanted to question Natalie but she was sleeping so peacefully, I let her he be. Instead, I replayed my memories of the previous night.

I remembered money being passed to Natalie. Lots of money. Money from Gilbert and Ray, and from Steve and Ben. There was also money from Frank as we were leaving. I wanted to ignore my fears. Were we paid for sex? I fought the thought. I tried to banish it from my mind. Was I a whore?

I was nearly in tears when realized Natalie was awake. She was watching me. I tried to hide my face. I reached for a tissue but she stopped me. She quieted my sobs with a piercing affectionate look and leaned her face toward mine. She slowly slipped her tongue to my cheek and licked my tears. She kissed me as tenderly as a mother kisses a baby and asked me to wait a moment before saying anything. I nodded and she stepped across the room to her purse. She carried it back to bed and lifted out a wad of cash. She counted out some amount, I don't know how much, and held it out to me. I wanted to spit on it.

"So it's true?" I asked starting to sniffle again.

"Yes."

"I'm a whore?"

"No," she answered sternly. "No one paid you for anything. I'm sharing my money with you because you deserve it. What you did, you did for pleasure and that's never selling yourself."

I broke down crying again. Natalie didn't try to stop me so I cried for a few minutes.

"Are you my pimp?" I asked.

"That's a harsh way of thinking," she said as she began to lay out the situation. "I do manage a string of T-girls. And I do get paid for my services. That's where I go every morning. I meet my girls and they give me my share of their earnings"

"How much is your share?"

"Fifty percent if I set up the date, twenty if it's their own client."

She held out the money again.

"That's what you earned last night. It includes a share of Frank's liquor sales. When anyone buys us drinks, Frank gives us a percentage."

I hesitated.

"Take it," Natalie said. "I know you need it."

"How much is there?"

"Four hundred dollars."

I didn't feel good about it but I took the money.

"I know this is a shock," Natalie continued. "At this stage I always give my girls a chance to back our."

"You've done this before?"

"Of course," she said, surprised by the question. I find all my girls this way. Most men are very willing to become women if you present it the right way."

She went on to explain that I wasn't yet ready to join her stable but she knew that with another week of training I would be the star of her group. But before she would spend another week with me, she wanted me to be sure. I had to go home and think things over. Leave her, and return to my old life. If I wanted to return, she would be waiting for me. She already had my male clothes in a shopping bag by the door. She said I should take them and anything else I wanted. Go home and make up my mind to continue or not.

I arrived at the apartment I shared with Tommy with the shopping bag of my male clothes and a small valise with the things Natalie had bought for me. I also had the $400 in my purse. I knocked on the door even though Tommy was expecting me. I had called and told him I was returning home with a surprise.

After the door swung open, Terry stood motionless. He knew it was me but he couldn't speak. He stared in disbelief. I was wearing a Boucle' gray tweed suit. The one- button top had a low cut V-neck line with pleated trim at the cuffs. The skirt was back zipped with a ruffled hem. It was above my knees, about mid-thigh, showing off my legs. On my feet were my favorite red five-inch heels. I know I looked fantastic; more sexy and feminine that 95% of all the women I saw from the taxi window as I rode over.

I think Terry's brain just could not process the fact that in only one week his cousin had somehow become a hot woman. The way he looked at me, almost drooling with his mouth open, he seemed to look as if he were ready to turn hetero. We might still have been standing there if Jay hadn't shouted from the other room.

"Is that Marshall?"

"Yes," Terry responded in a disembodied voice, not really sure.

"Can I come in?" I asked after another moment of silence had passed.

Terry still didn't respond. He just backed away from the door absent-mindedly. I dropped my packages in my bedroom and stepped into the living room.

"Hi Jay," I said in Marcia's voice.

"Holy shit!" was Jay's greeting to me.

It was at least twenty minutes before Jay and Terry could speak coherently. By then, they were seated on the sofa and I was opposite them in a cushiony chair. My hands were in my lap and my legs were crossed and pressed together at the knees. My ankles had a slight twist so that, my heels were on the flat on the floor side by side and under my ass. I sat up straight as a ramrod. Except for the fact that my skirt was very short and rode up nearly to my crotch, I must have looked like a very demure and proper woman. It amused me that they continued to stare. Their eyes never stopped going over me. First my legs, then my tits, my face and hair - each in turn. Then they would start over again in the other direction from the top to the bottom.

I finally became tired of their "wows" and "oh, my gods", I started the story. I told them everything that had happened after they left me in the bar. Suddenly their brains began working and they were full of questions. I answered every one. Including the big one.

"Yes," I admitted after think about it for a long time. "I did enjoy dressing this way. I did enjoy pleasing Natalie and the men that I had sex with. Yes. I did like being a woman."

They were both supportive, and being gay, neither one thought it odd that I would like sucking cock or being fucked up the ass. They would approve of whatever my decision was.

After a while Jay had to leave and we hugged good-bye more tenderly than we had ever before. Going out the door, Jay passed Terry's boyfriend Phil coming in. After the initial shock wore off, Phil opened a bottle of wine and as we drank it, I felt him leering at me. Terry seemed oblivious as he polished off the lion's share of the wine. The stares from Phil reminded me of the ogling that had gone on at Frank's club. It was kind of exciting that Phil was interested in me but I was uncomfortable with it going on while Terry was there. I finally excused myself and went to my room. I undressed, and although I had all my male clothes available and nearby in my closet, I chose to wear a black baby doll that I brought from Natalie's.

I suppose I knew what was going to happen and wearing the negligee was how I subconsciously gave in to the desire. The apartment had been quite for several hours but I hadn't slept at all. I was waiting for Phil. I knew he would come for me. Sure enough, I heard a sound at my door and then watched as it slowly open. Phil closed the door gently behind him and moved to the edge of my bed within a foot of my face. He was naked and the musky smell his crotch filled my nose and excited me.

"You're beautiful," he whispered. "What are you wearing?"

"I put on my sexy lingerie for you lover." I purred as I cupped his cock in my hand.

Phil gasped and stood motionless while I teased his cock to an erection. Soon he lowered himself on top of me and we kissed deeply. We inhaled each others tongues while his cock pressed against me. He asked if he could suck on my clit. The thought sent shivers through my body.

"You can suck on anything you please," I answered.

Phil kissed his way down my body stopping at my tits. He pushed the nightie aside and attacked my nipples with his tongue. They were very sensitive and I squirmed under his touch. Soon, his mouth was moving down again and he was guiding the hem of the baby-doll above my crotch. The sheer material tickled my cock and it jerked involuntarily. Phil slid both hands, palms up, under my ass, cupping my cheeks. My cock was stiff as a board and pointed at his mouth. Phil is large, about six foot and very muscular. I felt his arms tighten and I began to rise. He was lifting me off the bed - ass first. He was so strong that he easily lifted me. My back arched and my pelvis continued rising. My cock moved closer his mouth. I felt helpless but completely comfortable with his power.

I was in the air. I imagined myself being served on a platter. When Phil swallowed my cock, I came instantly. He continued sucking me while he held me in the air. My body bucked and spasmed as Phil vacuumed every ounce of cum from my dick. When he lowered me, he gently turned me onto my stomach and pushed my legs apart with his hands. He needn't have bothered. I happily spread my legs anticipating what would come next. I was not disappointed. Phil plunged his cum soaked tongue into my ass. I gasped, as he forced my own cum into me. He licked huge swaths of cum up and down my crack and behind my balls. By the time his prick was pressing against my hole I was aching to be fucked.

He plunged easily into me and began pumping furiously. I rocked and shimmied wanting to feel it all. I didn't want to miss even one inch of his shaft. Phil was large and strong. His strength was amazing. He lifted and spun me in any direction he desired. He bounced me up and down on his cock like I was a toy.

Soon he was cumming. His cock grew to an amazing size and pulsed wildly. He drove it deep into me and pushed his crotch forward while pulling me back against him. I came again.

We must have passed out because it was light when Terry came into the room. Phil was still lying on top of me, his morning wood still deep in my ass.

"Get out you slut!" Terry shrieked. "Get out of my house you slut!"

Terry started slapping Phil's back. Phil quickly jumped off me leaving me empty, but not sorry for what we had done. Terry kept yelling and slapping at Phil until Phil lost his temper and punched Terry knocking him down. He cursed, stepped over Terry and strode into their bedroom. Terry rose and looked at me disgustedly.

"I want you out of here," he said as he sheepishly followed Phil out.

I closed the door and began dressing in the sexiest outfit I had.

I closed the apartment door behind me knowing that I was closing the door on my old life. I had made up my mind to live as a woman no matter what terms Natalie demanded. I was in a cab heading back to Natalie when I realized that I had known it all along. I loved being an attractive woman. That was why I had flirted with Phil; why I enticed him into my bed. I wanted men to desire me. I liked using the power of sex as I pleased. It didn't matter that men were stronger or richer. I could control them with sex. I could make them cheat on their lovers or even betray they own morals. That was why I had stolen my cousin's boyfriend.

Natalie wasn't surprised to see me.

"They all come back," she said.

She warned me that we had much work to do before I went out on my own. We practiced dressing, make-up, walking, talking, and all the other womanly arts for the rest of the week. I sucked Natalie and she fucked me often. She put butt plugs in my ass. They grew larger and larger. She left them there nearly all the time. She said she was training me for the really big cocks. When I told her I couldn't wait to have my first really big cock, she smiled.

Soon the big night arrived. She called it my graduation. We stood in her closet and Natalie told me to pick anything I liked. I think she was surprised because I didn't hesitate. I knew the dress I wanted. I had seen it before and promised myself that I would wear it if I had the chance. It was sunflower yellow, made of stretch polyester and there were two holes cut in the sides to expose the hips and lower back. Red trim with dangling ties outlined the cutouts. The neckline was modest but the hem was short and slit very high. The combination of showing hip and thigh was deadly but it meant that I couldn't wear a garter belt because it would show through the cutouts. Natalie solved that problem by giving me a pair of elastic top thigh-high stockings. When I had slid them up my leg, they stayed snug around my thigh, hanging by themselves, two inches below my balls.

For shoes I chose a pair of strappy sandals with four-inch heels. I felt wonderful when I stepped into them, taller, sexier and ready for action. I stood and watched Natalie dress. I was green with envy when slipped on her pink bra with matching panties and garter belt. I craved to wear that garter with the lace and small-embroidered red flowers. I seriously considered changing my dress because I was so in love with the image of smooth sexy legs encased in stockings held up by garter straps with matching panties hiding a cock under their silky fabric. Being so fickle about my outfit made realize I was getting more like a woman every day.

Natalie slipped pink leather stilettos onto her feet before stepping into a pink dress reminiscent of Cyd Charise in a Fred Astair movie. It was chiffon and seemed to float on the air. When she spun, the dress twirled and the hem rose above her crotch, like Marilyn Monroe's dress being blown up by the passing subway train. The neck was cut in a deep V and the ultra-thin material layered the edges. The waist was tight but ripples of chiffon gave an illusion of a cushiony softness. She circled a string of pearls around her neck and was done. The sexiest, softest, and most alluring vision of pure beauty I'd seen in all my years. To look at her, was to understand that a beautiful woman can be soft, kind and gentle, yet at the same time she knows what men want and she wants to give it; but above all, she has to look pure no matter what.

"I think we should comb out your hair," Natalie said. "I think it's long enough. You shouldn't need the wig anymore."

As I pulled off the wig, Natalie grabbed a brush and began running it through my hair.

"Yes, it's going to be perfect."

She had me take off the dress again and she washed my hair in the sink. She blew it dry and brought me a hand held mirror. My hair was still quite short, but it was cute. She had gelled it and combed it straight back. It looked like a women's version of a boy's haircut. I couldn't make up my mind.

"I think I'd rather wear the wig," I said.

"Don't be silly. You look lovely. And besides, this is much more appropriate for where we're going tonight."

I looked at myself again and considered my new look.

"OK," I said. "A new look for a new life."

An hour later we were at a new club in the East Village. It was much different crowd than Frank's. The room was cramped and dark. The bar was old and the tables and chairs were cheap; like they had come second hand from a cafeteria. There was a 20-foot dance floor that was raised one step above the worn linoleum floor. It was noisy with the sound of disco music and yelling voices. There was a single dancer doing a sexy shimmy on the raised floor. Butch women in short haircuts and black leather surrounded her. They were shouting at her and holding out dollar bills. The woman was dressed in panties, bra, stockings and high heels. Her tits were huge and she often bent forward to allow the cheering women to stuff the bills between her tits or into her stockings or panties. It was like every titty bar I had ever been in, except here the sex crazed audience was women, and they were egging on another woman.

Natalie and I started across the room. Natalie nodded to the bartender, a woman over six feet tall wearing a black Harley Davidson tee shirt and black chinos. She was pretty but her hair was short and the muscles in her arms bulged. She stared at me as we passed. The hooting women noticed too and stared. Natalie and I were by far the most feminine girls in the place and I felt excited but also a bit afraid. Most of those girls were well muscled and could have done just about anything to me that they wanted to.

Natalie paid no attention. She led me to a seat right at the edge of the dance floor. There was a rail about three feet high between it and us. It wasn't strong enough or high enough to keep any one from falling off the dance floor, but if you were dancing and brushed against it, it would warn you that the edge was near.

Before we had sat down the shouting picked up again and the dancer responded by vigorously shaking her tits and ass. It drove the girls wild. I noticed there were several women sitting quietly at tables in back away from the dance floor. Must be the girl friends of the ones who are getting worked up by the dancer, I thought to myself.

Movement brought my attention back to the dancer. She was coming closer to us and soon was just across the rail. She bent down so we could slip a dollar between her tits I thought, but instead she leaned in and Natalie kissed her long and deep on the mouth. This really made the audience go nuts. Then she leaned toward me.

"Kiss her," Natalie ordered.

I did and cheers filled the room.

She spoke to me, "My name's Cyn."

"I'm Marcia," I answered.

Cyn leaned back and lifted her leg until she had hooked the high heel of her right shoe on the rail. Her legs were spread, giving Natalie and I a close view of her crotch. Just as I noticed the bulge and realized that Cyn was one of us, she pushed her panties aside and withdrew her cock from some sort of sling, which had held it tight between her legs. Released from its prison, Cyn's cock sprang from between her legs. It was large and erect and Natalie quickly swallowed it. She sucked it briefly to the cheers of the crowd and then looked at me as she let it slip out of her mouth.

"Suck," she said.

I looked at the cock, at Cyn, and at the audience. I even noticed the bartender looking on anxiously.

"Suck it," Natalie said again.

I opened my mouth and moved my head toward Cyn's cock. I closed my eyes as I wrapped my lips around her shaft and lost myself in the familiar salty musk taste. The cheers swelled and in a moment I was sucking Cyn's rock-hard cock as if on a stage. When I opened my eyes, the room was in frenzy. The girls were practically throwing their money onto the stage. They were licking their lips, shouting, and looking very horny. Cyn's was nearing an orgasm and the cheers became one.

"Cum, cum, cum," they chanted louder and louder.

The noise was deafening and it turned me on. I sucked and rubbed her ball and when I felt Cyn about to blow, I forced her as far down my throat as I could. It felt like she was shooting her load straight into my stomach.

I had never heard such loud screaming. There was even applause. Cyn's knees had buckled and she had nearly fallen over. She recovered and started picking up money from the floor.

"Now you suck Marcia," Natalie's voice boomed.

Cyn looked surprised and a little bit hurt but she got ready to do as Natalie had commanded.

"Sit back and spread your legs," she said to me.

I did and Natalie pushed my dress up over my crotch. There was more cheering from the girls when my erect cock appeared.

Cyn began to climb down from the dance for but Natalie stopped her.

"Stay up there."

Cyn squatted and leaned toward me.

"No," Natalie said. "Bend at the waist. Keep your ass up."

It took Cyn a minute but then she understood. She placed her hands on the rail and bending at the waist, lowered her mouth onto my cock. The women in the room cheered and I nearly lost it. Natalie saw how close I was to cumming and pinched me. The tweak snapped me back to some form of reality and with great concentration, I was able to prevent myself from spurting. When I was under control again, Natalie leaned close and kissed me passionately. At the same time, she fondled my breasts. I put my arms around her neck and sucked on her tongue. It was an amazing turn-on to have my cock deep in Cyn's mouth while Natalie's tongue was down my throat.

Natalie stood and brushed my shoulders as she passed behind me. I watched her step onto the stage and place her hands on Cyn's hips. Natalie pulled her crotch against Cyn's ass and moved in a very suggestive rhythm.

"Fuck her, fuck her," a woman shouted from the audience. Soon it became a chant picked up by the whole crowd.

Natalie, mimed fucking Cyn's ass and the women yelled even louder. She rotated her hips and thrust toward Cyn's ass. She did a small dance exactly like a stripper. All her movements were slow and deliberate and very suggestive. She slipped two fingers into the waistband of Cyn's panties. Cyn wiggled her ass, which helped Natalie get the panties down. Natalie squatted as she lowered them all the way to the floor. When she stood again, she licked up Cyn's body from her calf to her ass. The women were beside themselves.

"Fuck her, fuck her."

Natalie surveyed the crowd. She lifted her dress and hefted her cock out of her panties.

"You want me to fuck her?" she shouted to the crazed crowd.

"Yes," they answered in unison. "Fuck her."

"Then lets see some green," Natalie challenged.

I never saw so much money fly through the air. It fluttered all around the room. Crumpled wads of cash bounced off Cyn and Natalie.

"Alright," she said. "You've got it."

I don't know what was preventing me from cumming. I think I was too mesmerized by the show Natalie was putting on. She licked Cyn's ass to prep her and then plunged her cock in up to the hilt. The force of the thrust pushed Cyn into me but she never lost her cock-sucking rhythm. As Natalie pounded at her ass, I could hear Cyn start to moan. She was loud enough to hear over the chaotic crowd.

I don't know who came first. All I do know is, I shot my load into Cyn's mouth and grunted like a wild animal. Seconds later, Cyn screamed and I felt her body shudder. When I looked past her, Natalie was still pumping her ass and waving her hand over her head like a rodeo bull rider. She was slapping Cyn's ass and whooping giddily when she finally came. A huge smile grew on Cyn's face and she kissed me like a sister would.

"Natalie is the best fuck I ever had," she whispered to me.

Natalie walked to the edge of the stage and leaned over the rail where Cyn and I were silently sharing the knowledge that we were both completely and happily in Natalie's control.

"Now it's time to make some real money," she told us. "Hand me my purse."

She strode back to center stage and the crowd erupted in wild applause and cheers. She reached into her purse and pulled out two dildoes. She held them over her head and shouted to the crowd.

"Who want a piece of these two?"

There was a stampede to the stage as women practically knocked each other down to force their money on Natalie. She organized them into a haphazard line and they paid whatever she asked for. Cyn and I were watching from the side, a little afraid by the women's enthusiasm but also very turned on by their desire for us.

A young woman marched up to me after finishing doing business with Natalie. In her hand she held a nine-inch dildo. She took my hand and led me away. Her grip was powerful and she walked swiftly. I had trouble keeping up in my high heel sandals. She was my height with small tits. Her hair was dyed black and cut very short. She wore a black tee shirt, blue jeans and work boots. As we neared a table in the back of the room, I noticed a frail looking girl with long blond hair walking on a line to meet us.

"Get on the table and spread your legs," the dark haired one said when we reached the table.

It was a good solid table so I had no trouble. After she had pulled my panties down she took a tube of KY from Blondie and smeared some onto the dildo. Without any warm up, she lifted my ass with her left hand and slipped the dildo into my hole. It was cold and I let out a small gasp. She smiled and unhitched her pants.

"This is going to be good, Becka," she said to her friend. "You finger me while I fuck this bitch."

Becka positioned herself and began rubbing her friend's clit while the dark one worked the dildo in and out of my ass.

"I want to fuck you till you cum you bitch," she shouted at me. "I want to hear you cum."

Becka was doing her job well. The girl began moaning

"I'm fucking him Becka. Look how I'm fucking him," She snorted.

What Becka saw was me nearing a climax. My cock was pointed at the ceiling. It was a deep red color and it throbbed and twitched.

"I'm going to cum."

"I'm fucking him, I'm going to make him cum."

"I'm cumming," I screamed.

I spurted a small load and the dark girl came also. Becka kept working her clit and the girl's body shuddered. I think it was subconscious, but she kept pumping my ass keeping me writhing on the table.

When the girl had finished, she hitched up her pants and walked off without a word. Becka followed her silently.

They couldn't have been gone for more than a few seconds, when another woman, much larger, fat in fact, stepped between my legs. She grabbed the dildo, which still inside my hole, and began to plunge it in and out. I stared at her face while she fucked me. All I saw was anger. She was full of hate. I suppose that men had mistreated her and that she hated them for it. I could see she wasn't getting any physical pleasure from ramming the didlo into me. But I'm sure she felt that she was getting back at every man that had wronged her by mercilessly fucking my ass. She was a sexless beast and there was no way I would ever get turned on by her so I decided to fake it.

"Ohhhh, your cock is too big. It's too big. You're hurting me," I moaned loudly.

"Take it all you fucking slut," she spit. "Shut your mouth while I fuck you."

I writhed, pretending that she was giving me the best fuck of my life. I continued to act, torn between the pain and the pleasure and a grin cracked her face. That was her thing. If she thought I couldn't help being excited, in spite of the fear, she was happy. I finally faked and orgasm and I made it as loud and over the top as I could.

"Oh god, that was incredible," I confessed to her.

She gave the dildo one last shove and sneered, "All you sluts love it rough." Then she spun on her heels and walked off.

Another woman stepped up almost instantly. Again the hair was extremely short. She was very thin and had small tits. She wore a skin-tight tube top and black leather pants with high heel boots over them up to her knees.

"Get on all fours," she ordered.

I turned and lifted myself into a doggie position. She pushed my dress over my ass and pushed in the dildo. She did it gently. So slowly, the anticipation got me going again. And I heard her sigh.

"Oooo yes. That's good isn't it baby?" she asked sweetly. "We like that don't we?"

I did like it and I pushed my ass back to meet her soft forward thrusts.

"Not too fast honey," she cooed. "I like to take my time with sweet girls like you. I'm a big tease. I love to slide my big cock into a sweet pussy like yours and feel how it makes you crazy. You love my big cock, don't you sweet girl?"

"Yes I do. I love your big cock inside me."

I wasn't lying. I was very turned on.

"My big cock is going to make you cum. You can't help it. My big cock is too much for your sweet pussy."

I was feeling the orgasm building. I rocked myself forward and back, faster and faster. Feeling my excitement, she shifted speeds. The dildo was still moving slowly, but the strokes were strong and firm and deep. With the completion of each forward push, when the dildo was as deep into my ass as she could push it, she started to give it a twist. That sent me over the edge.

"Is my sweet pussy ready to cum? Cum for me sweet girl."

I wanted to cum for her. I wanted to cum as never before. As it turned out, it was the oddest orgasm of my life. There was no cum left in me. My cock spasmed and twitched and my body shook, my asshole tightened and I felt the dildo sliding in with more sensation than ever before. I humped it wildly. I grunted and snorted in a frenzy with a mad tingling feeling running over every inch of me. It was glorious. And then I collapsed, face forward, with my ass in the air and the woman returned to the ultra slow, rhythmic and gentle fucking motion that she had started me off with.

"Ohh, that's my sweet girl." was the last thing I heard before I crashed into unconsciousness.

Next: Chapter 5


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