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.
When I awoke, I was alone in bed. I threw off the covers and went looking for Natalie. I found her in the kitchen sipping coffee.
"You look so sexy in my nightie," she said as I stepped beside her and kissed her square on the lips.
I hadn't realized that I was still wearing the nightie. I felt so natural that I never even questioned it. And now that Natalie had pointed it out, I was glad that I still had it on.
"I feel sexy," I replied.
"You were fantastic last night. I wish we could jump right back into the bed but I have errands to run."
"Do you really have to go?"
The idea of being back in bed with Natalie was appealing to me too. I didn't want this escapade to end. Apparently Natalie didn't want it to end either.
"Why don't you wait for me here?" she suggested. I won't be too long and when I get back we'll pick up where we left off."
"Why not?" I thought. I had no place better to be.
I told Natalie that I'd be happy to wait for her and she stood.
"Come with me," she said and led me a door.
The door led to a room size closet full of women's clothes.
"While you're waiting, pick out something for me to wear tonight. I'm taking you out for dinner," and in a sterner voice added, "And choose something sexy for yourself."
She easily read the dumb look on my face.
"We're going out as girlfriends tonight," she explained.
I suppose it was silly of me to protest. I had been wearing the nightie all morning and that didn't seem to trouble me. In fact, I was enjoying it. Once again, it was as if Natalie could read my mind
"I know you like wearing my clothes," she said. "If you didn't, you'd be back in your jockeys now instead of mincing around in that wonderful nightie."
"I'm not mincing," I protested lamely.
"Maybe not, but you certainly are working it girl."
I couldn't argue with that. I was trying to turn Natalie on. I also wanted to do what pleased her. But I did explain that I had no concept of how to choose what to wear and I wasn't comfortable about going out dressed as a woman.
"Don't worry about passing, " she reassured. "I'll help you. Besides, I know a place where no one cares. And choosing an outfit is simple. Pick something for me. Then go back in the closet and pick another outfit you'd like to see me in. That one will be yours."
It did sound simple. I decided to trust Natalie. She could tell that I had accepted the plan so she kissed me and strode out of the apartment.
I returned to the kitchen and sat sipping coffee for a time. I replayed the situation in my head. Why was I resisting? Unconsciously, my hand fell to my lap and I began massaging my cock through the sheer material. The strokes were soft. My cock stiffened and I continued to rub myself on autopilot.Soon I realized how excited I was. I stopped stroking myself and walked to Natalie's closet.
Inside the closet I marveled at the sheer volume of clothes. I've seen stores with less stock than Natalie's closet. Hanging on the right was an eight-foot long row of dresses, skirts and blouses. I brushed them with my hand as I walked past. On the left was a row of coats, gowns and sweaters. Then I saw the shoes. The back wall was lined with shelves from floor to ceiling and shoes of every style and every color rested there calling my name. I floated toward them and lifted a high heel pump and began reeling as dormant memories flooded back to me. My love, my obsession, with high heels was returning.
I don't recall why or when I became enchanted with heels. But I do remember when I first acted on the feeling. I was a pre-teen, probably just beginning puberty. I was alone in the house and I mustered all my courage and crept to my mother's bedroom. I slid open her closet door and admired her shoes. I lifted a pair of Mom's pumps and caressed them. The breath went out of me as I slipped them onto my bare feet. I had my first orgasm that day, standing in three-inch heels looking at myself in a mirror on my Mom's closet door. I had continued to wear Mom's shoes and jerk off while doing it every chance I had until I left home. After that, I had not worn heels again and I guess I had repressed the memories. But they all came flooding back that morning when I lifted Natalie's shoes.
I was shaking with anticipation. I lifted my foot and lowered the shoe. I pointed my toe toward it and prayed the shoe was large enough. It slipped on perfectly. I stood, bent slightly, as I slipped on the second shoe. I stood straight up and it felt marvelous. I was suddenly three inches taller, my claves were tight and my butt was firm. I threw out my chest and stepped confidently to the mirror. I turned sideways and admired my new, shapely legs that stretched all the way from the ground to the hem of the red nightie.
As wonderful as I felt, something was wrong.
"Pantyhose," I thought. "I need pantyhose.
I remembered that as a teenager I had eventually begun wearing Mom's pantyhose. I hoped Natalie had a pair. I searched the lingerie drawers in the closet but couldn't find any. I did find stockings and decided that they would be just as good. They turned out to be even better. I slipped off the shoes and put on the stockings. With the stockings on, the pumps slipped on even easier. I walked around in them a little until the stockings fell down.
"Garters," I thought. "I need garters."
I had seen them while looking for the pantyhose. I figured out how to wear them and attach the stockings. I tried on several different pair of Natalie's high heels and soon I was striding around her apartment like I had been born in them. The next time I passed a mirror I admired myself. I looked good in the coral-colored heels, dark stockings and red nightie, but I realized I could improve the picture. The heels clicked as I hastened to the bedroom. I reseated the wig from last night on my head and had another look at myself.
"Fantastic," was the word that came into my mind.
I swished around the house wishing that Natalie would come home. I did the dishes, swept the floor and even made a lunch. When I heard Natalie's key in the door, I readied myself. When the door closed behind her I stepped out and presented myself.
"Wow," she said. "You have made a lot of progress this morning but we still have a lot of work to do."
I think she saw my disappointment because very quickly she added, "But not until after I fuck my favorite girl."
And that's what she did.
This time it was even better. I still had on my stockings and heels and I felt totally feminine. I had sucked Natalie's cock and Natalie had fucked my ass but Natalie had not sucked me or allowed me to fuck her. In fact I never fucked Natalie again. But at the time, that didn't matter. I loved the feeling of Natalie inside me. After she came and her cock shriveled, I cried and pleaded for more. Natalie promised that there was a lot more to come.
Afterwards, I realized I was different. As Natalie prepared me for "going out" I was light-headed. She shaved all the hair from my body and massaged me with moisturizer while my head was in the clouds. She helped me into matching black panties and bra and slipped glycerin breasts into the 34C cups. My stockings and garters returned before she helped me step into a conservative blue dress with a slightly revealing V-neck. Make-up, three-inch matching heels and the wig followed. When I saw myself in the mirror, I was shocked. I knew that I'd have no trouble passing. I was lovely.
Natalie dressed quickly in a yellow mini-dress with matching high heel boots. She hurried me out the door and into a taxi. The driver ogled us the whole ride to the Village. He deposited us on Hudson Street and we strutted into a restaurant named "Ms. Franks."
The staff knew Natalie and greeted her warmly. Because I was with her, I was given special treatment also. The hostess hugged me. The waitress kissed my cheek. Even the owner, Frank, came to our table to say hello. As we sat sipping wine, I realized that the restaurant was full of girls like Natalie and myself and I looked better than many of them. I was proud of my looks and I wanted to show off. I asked Natalie to sit beside me. She moved beside me on the settee and I kissed her deeply.
"Thank you for tonight," I said.
"It's my pleasure," was her response.
We continued to neck all during the meal drawing many jealous looks. I mentioned to Natalie that many of the people in the restaurant wanted what we had. She surprised me by saying that it was what she had that the others wanted. She said that everyone knew that Natalie would be fucking me later tonight and that they all wished they could be her. The thought of being that desirable made me instantly aroused and I asked Natalie to take me home. We were all over each other in the cab back up-town. The driver was barely able to keep his eyes on the road. When he dropped us at Natalie's place, I thought he was going to tip up. He did ask to come upstairs with us but Natalie said I wasn't ready yet. It was a revealing thing for her to say but I didn't understand then.
Once upstairs, Natalie ordered me to suck her cock in a soft voice. I fell to my knees and pleasured her happily. After twenty minutes Natalie led me to her bed and removed my dress. She left all the underwear and shoes on me and told me to get onto all fours. Natalie's hem was up around her waist and she snugged up behind me. She rubbed her hard cock against my ass.
"Is this what you want slut?" she demanded.
"Yes. Please fuck me with your beautiful cock," I begged.
She wasn't ready to fuck yet. She wanted to eat my ass. She tongue fucked me until I thought I would burst. Then in a smooth motion she rammed her cock into me. I came instantly but she was only getting started. She hammered me for half an hour before I felt her climax. When she did cum, she filled me with gallons. Yet, she kept pumping. She kept it up for another ten minutes and brought me to the most explosive, intense orgasm of my life. It was then that I knew that Natalie was a lovemaking machine and that she had changed my life forever.