Natalies Business

By Marcia Fredricks

Published on Jul 15, 2004

Transgender

Chapter 1 - The Pick Up

New York in 1975 was a great place to live. Sex was everywhere. I'm not saying I was a great stud. I'm slightly built and there was plenty of competition from tall, well-built, stylish Yuppies. But I still did all right with the ladies. I got my fair share of pussy. If it wasn't pussy you were after, there was even more sex available. I was straight - but my roommate wasn't. I shared an apartment with my gay cousin. Tommy got sex whenever he wanted. If he decided he was horney, any time of the day or night, all he had to do was go to the gay bookstore, movies, or baths and he could get laid or a blow-job. I was a bit jealous. I didn't want to be gay. But one thing was certain. If I had been gay, I wouldn't have spent weekend nights in pick-up bars squandering my meager pay on drinks for cock-teasing girls.

I didn't mind living with a gay man. Tommy was my age. We had grown up together. This was the first time on our own after college for both of us. We had a large two-bedroom apartment and what went on behind closed doors was no problem. Tommy's friends were cool and quit hitting on me when they were told I was straight and intended to stay that way. Also, my brother was gay. So I was comfortable in their company. I had no problem hanging with them.

One Friday night my brother Jay came over. He, Tommy, and I had several drinks and they convinced me to go out with them before I hit my usual singles spot. They wanted to go to a gay bar. I argued against it for a while but finally gave in. Twenty minutes later we were sipping our first round at a table in a very straight looking gay bar. There were more men than women there, but the women that were there, were extremely good looking. A steady stream of men came and went from our table. Jay and Tommy flirted while I made it clear that I wasn't interested. Every one was fine with my choice. They chatted politely and left happily. It was a relaxed atmosphere - different than I was used to in the normal meat market atmosphere of singles bars. I felt comfortable, so I stayed. Beside, I had my eye on a woman that had come in and sat at the bar about an hour after we had arrived. She was stunning.

I had always had a crush on Natalie Wood - the actress. This woman was her double. After looking at a woman's face, I always check the feet next. I want to see what style of shoes she's wearing. Sometimes I check the shoes even before her face. This one thrilled me. She had on black high heel pumps that were at least four inches. She also had on black stockings and a tight black mini-dress. She was showing a lot of very choice leg. Her dress was backless with a scoop neck, bare shoulders and long sleeves. I was mesmerized.

Over the course of the next two hours she sat alone. Not that people didn't approach her - both men and women - she simply shooed them away very quickly. I didn't understand why she was there. She just sat there all alone, ignoring her surroundings, sipping wine and refusing all comers.

Finally, Tommy and Jay had made their pick ups. Both were ready to leave and were surprised when I told them I planned to stay. I nodded toward the stunning woman at the bar. Neither one knew her. They wished me luck and left. I meandered to the bar and stood between her an empty stool.

"I'm Marshall", I said to her, "can I buy you a drink?"

She lifted her glass and twirled the red liquid inside - showing me she didn't need another. I turned to go but she stopped me by grabbing my sleeve.

"Don't go," she purred. "I'll be ready for another in a few minutes."

I smiled broadly and sat on the stool that so many had failed to occupy before. The bartender stepped up and gave me a knowing grin. I ordered my drink. When he left, the woman turned to me. We gazed into each other's eyes.

"My name is Natalie," she said and my jaw dropped. "I know. You had a crush on Natalie Wood", she said. I nodded my head.

"So many men do."

"You could be her twin," I stated the obvious.

"I'm so pleased you think so".

We chatted a bit more. Then she waggled her empty glass

"I'm ready," she said. I motioned for the bar tender.

"Do a shot with me?" Natalie asked.

"Sure. Shot of what?"

"Anything."

I ordered two shots of scotch.

"I have a theory about drinking shots," she confided.

When I asked what the theory was, she put a hand on my thigh and said, "You'll find out later."

The drinks arrived. We lifted the thick glasses and Natalie whispered something to herself that I couldn't make out but I'm certain she referred to me and to openness to new things. We tapped our glasses and downed the shots. Natalie slammed her's down on the bar, grabbed me behind the neck and forcefully pulled my face to hers. It was a passionate kiss; deep, long, hard, and desperate. I usual avoid public displays, but I was delirious. Our tongues danced and we pulled together tighter. Our kiss seemed to last for hours and when it ended every person in the bar was staring at us.

"I'm ready to go," Natalie said softly.

I paid the bill and followed her out into the night.

"My place is just around the corner," she said.

On the street in front of her building, she asked me to kiss her again. This time, as our tongues mingled, we pressed our bodies together. Her breasts pressed against me and my cock stiffened. I felt her hand on my ass pulling me closer. I ground my cock against her, placed my hand on her ass and squeezed gently. She cooed.

"Why me," I asked when we took a breath. "You shot down everyone else all night long. I didn't think I had a chance with you."

She took my hand and led me up the steps of her brownstone.

"Silly boy," she scolded. I knew you were the right one the first moment I saw you. I was going to tackle you if you didn't stop on your way out."

Inside the apartment, Natalie pointed to her liquor. "Pour some more shots," she ordered. I did as I was told. After we drank, Natalie repeated her whispered toast.

What's that?" I asked.

"It's a kind of prayer."

She stepped closer and took the glass from my hand. She placed it on a table and wrapped her arms around me.

"I'm praying that you are a man who's kind," she trailed off as she kissed me lightly on the lips, "understanding," more kisses, "willing to try new things," she nibbled my neck, "generous," she pushed me back gently until my legs touched a sofa, "horny as hell," she guided me down and lay on top of me, "and will fuck all night."

She slithered her way up my body until she straddled my crotch.

"Are you ready for me?" she was nearly growling.

I was barely able to answer.

"Yes."

Natalie opened my belt and unzipped my jeans. She tugged my pants down. My underwear slid off with the jeans. She grabbed my stiff cock and began an amazing blowjob. Her red lips slid up and down my shaft and she sucked like there was more scotch inside. She licked my balls and teased me with both tongue and fingers in that wonderful spot between balls and asshole. She kneaded my ass cheeks and spread them. Still sucking my rod, she fingered my asshole. I guessed that was one of the new things she had prayed for. It felt great and my cock got even harder. Then she slipped her finger into my hole. I made a sound like never before and shot a load of cum into her mouth. She swallowed it and climbed back up on me. She kissed me and forced some of my cum into my mouth.

"Why not," I thought.

I accepted her gift by sucking her tongue as far down my throat as I could. When we had no breath left, our lips parted.

"Hooray for new things," I said.

"I'm so happy you liked that," she said smiling. "I'm going to change. When I get back I want you hard and naked." Then she stood and strode out of the room.

When she returned, I was naked but not hard. However, one look at Natalie turned my cock rigid again. She was absolutely gorgeous. She was by far the prettiest girl I had ever been with and in a black lace corset with matching garters and stockings and four inch black high heels, she was also the most sexily dressed. She lingered in the doorway.

"If you're ready to fuck, get in here," she whispered across the room.

That was more invitation that I needed. I quickly stepped past her into the bedroom. The lights were low. I couldn't see but I heard the tap of her heels as she came to the bed. I felt her lie beside me.

"I have my period but I need you inside me. Would you please fuck my ass?"

That was another invitation I did not need repeated. I kissed her and she again went down on my cock. I pulled her off and started sucking her tits. She removed a tube of KY from a night table drawer. A palm-full of lubricant oozed into her hand and then greased my cock. I was ready to fuck her but the pleasure of her hand gliding up and down on my dick kept me paralyzed. I was whimpering - ready to cum - when she stopped and turned her ass toward me. I climbed to my knees and lubed her hole with my cock. Her moan, just from the touch of the tip of my dick was nothing compared to the sound she made as I pushed into her. She was tight and warm and I was in heaven as I slid slowly into her ass.

I pushed softly, and in a single long slow motion that seemed like an eternity, I pressed my full length completely into her. I began pumping - slowly - letting the low slurping sound mix with her gurgling moans.

Natalie's excitement was growing. She made sounds that I had never heard - like animal noises. I was going mad. I began humping faster and harder. I began making breathy sounds too. I reached for her tits. I cupped them in my palms and tweaked her nipples. She bucked wildly. I rubbed her tits faster making circles around them, all the while sliding my shaft in and out at a breakneck pace.

I slid my hands down from her chest to her stomach. I guess my intent was to massage her clit. But when my hand moved lower she screamed.

"No - I have my --"

She was too late. I had reached for her pussy and come up with a hand full of cock and balls.

The shock shriveled my erection to kiddie size instantly. But before I could separate myself from her, she grabbed my arms and pulled them tightly around herself. She was strong. I couldn't pull away. She held me firmly, pressed tight against her body.

"Don't speak. Don't move" she said, "Just lay on top of me for a minute. Then you can go if you want to."

I paused, my limp dick still in her ass. She continued in a reassuring voice.

"What's the problem? Don't I look like a woman? Don't I feel like a woman? Don't I smell like a woman?"

When I didn't answer, she asked again. "Don't I fuck like a woman?"

My dick began to stir.

"Yes - that's it. Kiss my neck. Smell me behind the ear."

I did as I was told. My dick was definitely hardening.

"Ohhh... I feel your cock in me. It's so big and hard. Please keep fucking me. I need you to fuck me hard."

That was it. I was back to full strength and didn't care who or what I was fucking. I began pumping her again and we were quickly back in a wild frenzy.

"Stop." Natalie said suddenly.

I did and she took my hands in hers and guided them to her cock.

"I have to cum before you do."

She held my hands tightly and slid them up and down on her cock. It barely occurred to me that I was jerking Natalie off. With my cock up her ass, her dick seemed an extension of my own. It almost felt like I was beating myself off. Soon her breathing was heavy and I could feel her ass contracting around my cock. Her ass gyrated in rhythm to the motion of my hand on her cock. Its forward and back motion slowed as my hand did. If I sped up, she humped me faster. When I concentrated on her dick's head, slowly drawing circles around the hole, she arched her back, squeezed tight, and ground her butt against the base of my cock.

"I'm going to cum," she announced in a guttural slur. "Make me come - oh please let me cum."

I pumped her dick as fast as I could. Her ass pistoned my cock.

"I'm cumming," she yelled.

I felt her warm sticky cum spreading over my hands. Natalie fell forward onto her forearms. He ass, still impaled on my dick, stayed in position but I freaked a little. I was desperate to wipe my hands clean. I did so on the sheet and lost my fucking rhythm. Natalie came to the rescue by restarting her humping. She kept my cock sliding in and out during my lapse. Quickly, I recovered my senses and started to pound her once again.

"Turn me over," she said, I want to see your face."

We managed to rotate her over onto her back while keeping my cock deep in her hole.

"Oh yes, that's it baby. Fuck me hard."

She grunted with each deep thrust. I was on the brink of orgasm. I was breathing hard and my mouth was open. I must not have been looking, because I suddenly felt Natalie's finger slip into my mouth. I don't know what I was thinking (after all, it was a pretty passionate moment) but I closed my lips around her finger and let Natalie fuck my mouth with her cum coated finger. Her cum was more delicate than my own - not as salty - almost creamy.

I was about to cum when she pushed in a second finger. I eagerly twirled my tongue around it. Then, as I came in a tremendous orgasm, an image of Natalie's cock fucking my mouth burned into my imagination.

It was more than a few moments before I recovered. My dick popped out of Natalie's ass and I managed to roll onto my side next to her. We lay still, not even attempting to speak. When our breath finally returned to normal, we were a couple of chatterboxes. We agreed that we had just had the best sex ever and that we couldn't wait for more. Natalie suggested we clean up. She thought taking a bath together would be fun. She skipped toward the bathroom and I followed. I grabbed for her ass playfully. She giggled and pulled away. I was on a cloud. I felt that feeling you get when you're starting a relationship and all you have is wonderful expectations. I hadn't forgotten that Natalie was a transsexual - I was ignoring it and I was floating on air.

We sat facing each other in the bubble filled tub. I reached toward Natalie and cupped her tits. We kissed. She fondled my dick. We necked. After a few minutes my cock began to harden again. Natalie stopped kissing me and lathered my chest with soap. She told me to stand. When I did she soaped my legs and balls.

"Turn around," she ordered.

I turned my back toward her and she lathered my ass. She began working soap into my crack. It felt good. I knelt a little, spreading my legs. She worked a finger into my hole. I enjoyed the feeling and wanted more. I got my wish. Natalie stood and pushed her index finger as deep as it could go. I let out a soft groan.

"You like that baby," she asked.

"Yes." I responded as if in a trance. She wiggled the finger inside me.

"Isn't it nice?" she coaxed.

"More," I said, still in a trance.

She slid a second finger into me and began working them in and out.

"Ohhhhh," I moaned louder.

She reached around me with her free hand and wrapped it around my cock. The finger fucking was doing wonders and in a very short time I came in Natalie's hand. She acted surprised.

"Goodness. You are a sex fiend," she exclaimed. "Sit down and rinse yourself while I finish myself off."

I lowered myself to the edge of the tub and sat. I stared at Natalie while I dried my hair. Natalie soaped herself, paying careful attention to her tits, cock, and balls. She gave herself a large erection but didn't finish herself off. Instead she sat, rinsed, and stood again. She grabbed my towel and began drying. She started with her hair and worked down to her shoulders and arms. The motion of her body as she patted dry caused her dick to swing. As I stared, that image of her cock in my mouth flashed in my mind. I concentrated on her body - full round tits, flat firm stomach, and a very beautiful semi-erect cock. I suddenly wanted that cock in my mouth.

I slipped to my knees and crawled to her. I reached out and cradled her cock and balls in my hands. I look up - past her tits. Natalie grinned like a Cheshire cat. I moved my mouth toward her rod, pushed my tongue out and licked it. Her cock stiffened and brushed my cheek. I wrapped my fingers around her cock and closed my lips around it. I moved my head forward and back in the manner that numerous girls had done to me. Natalie pushed my head away.

"That's terrible," she said. "Come with me".

She took my hand and led me back to the bedroom where she opened a drawer and removed a sheer red nightie.

"Arms up," she commanded.

I raised my arms and Natalie slid the teddy onto me. She turned me toward a mirror.

"Look how cute you are."

She left me peering at my reflection while she stepped into a closet. The sexy lingerie I was wearing fascinated me. Delicate spaghetti straps crossed my shoulders. Though my breasts didn't fill the cups of the teddy, they did fit into the proper space. The hem of the skirt ended just below my ass and billowed up as I spun to see myself from behind.

Natalie returned with a blond wig, which she placed, on my head. Lightly waved honey yellow hair fell just to my shoulders. I was mesmerized by the change. I looked like a girl. It's hard to describe how I felt. But one thing was certain - I didn't feel like myself.

Natalie stepped between the mirror and me. She placed her hands on my shoulders and guided me to my knees.

"Imagine yourself a beautiful girl. And your favorite thing in the world is to suck cock."

I looked up at her kind smile.

"I know you're going to be great at it," she reassured me.

My gaze returned to her cock just inches from my face. I closed my eyes and in my mind I pictured myself a beautiful girl in a sexy red nightie. I opened my mouth and took Natalie's cock into it. I caressed her balls and thighs and swirled my tongue around her hardening dick. I kissed, sucked, and nibbled it. I soaked it in my saliva. I wrapped a hand around the hard shaft and stroked it. In my mind I was a girl and all I wanted to do was to make that cock spurt its load into my mouth.

I deep-throated Natalie like an expert. My hands roamed her thighs, ass, and stomach. When they wandered up to her tits, she moaned. But that didn't fit my cock sucking mental picture (tits and cocks don't exist on one body) so both hands returned to my main objective - her cock.

With my face buried in Natalie's crotch, I was stimulated to work even harder by the odor of her sex. Musky and rich smells wafted off her like something unmentionable baking. I was fucking my face with Natalie's hard cock. I was doing it - me - Natalie was just the means to an end. And that end was rich creamy cum oozing down my throat and trickling from my mouth. The thought of it made me crazy. I pistoned up and down on her dick. She groaned. I knew she was close to cumming. I intensified the action. I grunted like an animal. I slurped like a fiend.

When Natalie came, it was an eruption. Her knees buckled. She yelled. She bucked. But I kept myself glued to her cock. Her body shuddered and her cock spasmed. I kept sucking for several moments until I had pulled every drop of cum from her worn out member.

"My god," she final managed to gasp. "That was the best blow-job ever." She knelt down and kissed me tenderly. "I'm exhausted."

We crawled into bed and settled into each other's arms. The last thing I was conscious of that night was feeling my cock pressed against Natalie's ass and her delicious smell as I nuzzled her from behind.

Chapter 2 - Becoming Marcia (preview)

The morning dawned cool, crisp, and with Natalie's hand between my thighs. I was lying on my stomach and I felt her hand caressing my balls from behind. Memories of the previous night came flooding back and I spread my legs so Natalie had easier access to my crotch. I felt her weight shift. She raised herself over me and kissed the back of my neck.

"You made me so happy last night. I can't wait to fuck you."

I was still a bit groggy and didn't register what she had said but even if I had, I could have never resisted after her next surprise. Natalie kissed her way down my back to my ass. She pushed my legs apart and knelt between them. She flipped the hem of my teddy up, lowered her face to my ass and pressed her tongue to my hole. The touch was electric. A sexual charge centered inside my ass-hole shot through me in all directions. I shuddered. Natalie continued flicking her tongue over my sphincter and I responded by making noises that didn't sound human. I spread my legs, grabbed my cheeks and spread them too. Natalie saw I was ready and pushed her lips tight against me. It felt like she had created some sort of vacuum and was sucking my hole into her mouth at the same time she was pushing her tongue into me - penetrating my ass - tongue fucking me.

There was more electricity and animal noises. Her tongue was strong. She worked it in and out of me. She reamed my hole and plunged it in again. Suddenly she stopped. Her weight lifted. She was climbing off me.

"Don't stop," I cried. "Please don't stop."

Before I had finished pleading, I felt Natalie's weight again pressing between my splayed legs. A cool sensation on my hole replaced Natalie's warm tongue. Then something large was pressing against it. Slowly my hole opened and what I hoped was Natalie's cock, was moving into me. I don't think I breathed as I concentrated on the wonderful feeling of being filled up. It was Natalie's cock. She whispered gently as she entered me. She offered reassuring soft promises of pleasure that were unnecessary. I loved the feeling. I anticipated the addition of each new millimeter of cock sliding easily into my ass.

"This is what getting fucked is like," I thought. "Why did I wait so long?"

I felt in some kind of heightened state of sensitivity. Everything seemed like slow motion. I relished every quiver and ripple of Natalie's cock. I felt each bump, each ridge of skin and muscle. My asshole molded to her shape as each additional bit of her pushed into me. When she stopped, I was disappointed she wasn't bigger. But soon she started to rock softly back and forth and I knew she was big enough. As she rocked, she also pulled in and out very slightly. She was teasing me. Building up my desire.

"God she was a fantastic lover."

In no time I was pushing my ass to me her strokes and grinding myself against her cock. Natalie moved faster now. Pulling out further and slamming into me harder and harder. Her balls slapped against my ass. I was going crazy. I cried for her to fuck me. I wanted her cock to fill me. I wanted her to cum inside me. I wanted to cum. Natalie dictated the rhythm. I was on my knees. I reached between my legs and tickled her balls. Natalie's cock grew to an amazing size. I felt it seize and shudder. Warmth filled my hole but Natalie kept slamming her huge pole into me. It slipped and slid, now that her cum had lubed me again. I felt it dribbling down my leg and on my balls. Natalie circled my cock with her thumb and finger and stroked it while she kept her dick pounding in and out of me. It was time for me to blow. No more holding back. The pleasure, the thrill, the fucking was too much to stand. I came harder that I ever had before. I may even have cried.

Natalie sensed it and stopped pumping. She pushed her cock as deep as she could into me and just held it there. I collapsed with her on top of me. I soon fell asleep with her cock still inside me.

Please email me with comments marcia_fredricks@yahoo.com

I have ideas for more but I want to know they're wanted.

Next: Chapter 2


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