My Best Friend The Tranny

I went over to Steve's house. It was the beginning of our last free summer before we had to go to college and get real jobs. I wondered why he had not called me yet. His parents were not at home and we were a couple of 18 year old, healthy all American males.

The door of his house was open, but no one was around. I called him as I walked into the house. There was no answer. I went up the stairs. The bathroom door was closed. I knocked on it, not wanting to walk in on his older sister. There was no answer. I opened the door.

Steve stood in front of me. His body was hairless. He had long, black hair, a pair of nylons, panties and a bra on. His lips were bright red, his face glistened with makeup, his eyebrows, dark and slim. He had a shameful expression on his face.

"Don't tell anyone," he said in a feminine voice.

"Dude," I was horrified, "what are you doing?" The smell of perfume was almost overpowering.

"I'm so ashamed," he sobbed like a woman.

"Dude, it's all right," I said, stopping myself from reaching out to him. He spread his arms helplessly, I felt like I had to grab him. I was holding him close to me, the smell of perfume, his feminine features, I could not believe I was looking at his mouth like I wanted to kiss it. I looked at his pretty face, I felt like I could not help it, I pulled him closer and brushed his lips with mine. He looked at me, cupping my face in his hands, he kissed me hard. My cock sprang to life as we began kissing. This was so wrong, he was a guy in make up and panties, and I was kissing him, rolling around on the bathroom floor.

"Take your clothes off," he said.

I should not have. But I did, I wanted him badly. I stood naked in front of him, his hard cock protruded through his panties. We stroked each other, he finally dropped to his knees and began to suck my cock, and I loved it. He sucked hard, suddenly his lips were against my balls, and he had deep throated me. The sensation was incredible. I could not hold back and I came harder than I ever had before.

He stood up to face me, my cum on his mouth, he leaned into me and kissed me, I tasted my own cum on his lips and in his mouth. I was now hot to taste his cock, and I licked down his chest, stopping for a few moments at his nipples, sucking each one into my mouth, then on to his thick cock. I stared at it, then tried to put my whole mouth over it, gagging for a moment, I heard girlish giggling as I finally figured out how to put it in my mouth. I sucked it, licked it, sucked his balls, it was all so good I could not believe how great it was.

Suddenly his cock began to spasm in my mouth. He pulled it out and his cum shot all over my face, I heard more girlish giggling and I realized it was not Steve. I jumped up.

Behind the shower curtain, filming everything with a camcorder, was Steve's sister, Jennifer. She was a hot college girl. Really hot. She looked like a model. Her long, blonde hair, thin bod with c breasts were killer. She stood laughing at my face, full of her brother's cum.

"Hi girls," she laughed.

"What's going on?" I gasped, "Steve, what is this?"

"Don't cry honey," she smiled sadly at me, "poor Stevie had no choice, I caught him on tape, wearing my finer things," she smiled wickedly, "so he had to do exactly as I told him, or her," she giggled.

"What are you going to do with that tape?" I asked, bewildered.

"Oh, nothing," she sighed, "if you two girls do exactly as I say. And by the way, don't even think of beating me up and taking the tape, my girlfriends are on their way over, after a stop at the store, and we have a lovely day planned for you girls," she giggled. "Now clean up, and Stevie, help your girlfriend there with his hair problem.

"What hair problem?" I asked as she left the bathroom, "Steve, what's going on?"

He smiled, averting his eyes from mine as he began spreading Nair on my body. It began to tingle, almost burning, "Hold still," he finally looked into my eyes, "we're going to have fun today."

Soon after he was finished with the Nair, he put me in the shower, which washed away all of my hair. It did feel pretty cool, my nipples were getting hard. He handed me a pink t-shirt, which almost came down to my nuts. My pants were gone. This was not funny anymore.

"Dude, where are my clothes?" I asked.

"You don't need them right now," Steve said in his fem voice.

"Hi ladies," Jennifer burst into the room, "oh don't you clean up nice Donny, but for the rest of the day, you will be referred to as Donna," she paused, lighting a cigarette and offering one to me. I said no, but she insisted. "As my girlfriends, you smoke," lit our cigarettes, telling us how to smoke like ladies, how to tease men with it. I wondered what the hell was going on. The three women she called her friends were at the door, they looked even older than she did, but they were hot looking also.

"These look good," smiled the one with curly brown hair. I felt like a piece of meat on display at the store, they looked us over, bringing out make up kits and going to work on me. It was an erotic feeling, having these hot women working on me, but where the hell would this end up? I was soon looking in the mirror at my fem self, attractive with long, red hair.

In Jennifer's bedroom, Steve and I put on sexy lingerie and several different outfits before the women were happy with our appearance. Of course, Jennifer videotaped everything.

Okay, it should be over. We had been humiliated. Sure, Jennifer could blackmail me, but I should be able to get back to reality now.

"Road trip," Jennifer said, looking at us happily.

"What?" I asked, horrified.

"Road trip, what about it girls," the other three asked eagerly, looking at us for approval.

Stevie nodded his head eagerly. I assumed that I had no real choice, so I agreed.

Giggling, the girls led us out to their convertible. It was a 2002 Ford Mustang, bright red. Under other circumstances, I would be honored to be riding in it. I was caught between the erotic feelings of wearing the women's clothing, and being out in public where I could be seen by anyone who knew me. I was nervously smoking as we rode down Route 1 in Sussex County.

The girls talked to Stevie and I as if we were women like they were. Soon, even I was happy to be one of them, laughing and joking, talking about hot looking men and oral sex.

Two hours later, we pulled into an old farm house in the backwoods area of Sussex County. We got out of the car and walked into the weathered, old farmhouse. It appeared to be a crumbling structure, and I began to wonder what indignity would come next.

Inside the door of the falling down farmhouse, was a beautiful lobby. Antiques, artwork and a brightly painted area made me realize that the front was merely a façade, the inside was a rebuilt area, with old style decorating. We were led into a small, yet tastefully decorated office.

Behind an antique, oak desk sat a beautiful, middle aged woman. Blonde, her long hair tied in a pony tail, her lips a delicate pink, her eyeliner soft, her eyebrows thin and dark. She smiled at us.

"Welcome Stevie," she smiled at him, "and Donna," she smiled at me, motioning us both to sit on the chairs in front of her desk.

I nervously tried to figure out how to sit down properly in my mini skirt.

"I am Sherrie Lynn," she smiled, "I am happy to tell you that you have been selected from a number of people for a very special opportunity."

Are you kidding? I wondered. In a very short time, I have discovered that I like to suck cock and that I enjoy wearing women's clothes and behaving like a woman. What great honor was I being selected for now, a lobotomy?

"I see the puzzled look on your sweet faces," she sympathized, "but our methods can be a little out there," she laughed kindly. "So many men come here to find the company of what we call, 'she males,' and we always have a couple on staff, young, pretty, cocks and titties."

Was this whole thing some kind of joke?

"No, it's not some kind of joke," she looked directly at me, "let me run the figures past you first, one thousand dollars per week cash, that is from me, that does not count your tips, and you will get tips or the customer will not be allowed back, you can do this for about two to five years before you either don't like it anymore or just do not look that good as a woman anymore."

I could not believe what she was saying. She was offering us jobs as prostitutes. Sure, one thousand dollars a week was nothing to sneeze at, and I had enjoyed sucking cock and the clothes, but every day might be a bit too much.

"Our doctor will administer the estrogen, we've figured out a good formula that gets you nice titties, great shining skin and nice, girly voices," she smiled, "without stopping your Canon from firing, if you take my meaning."

I looked at Steve, he was smiling at me.

"If you do not like my generous offer," she continued, "you probably won't want to tell anyone about us, because if you do, people you know might see your cross dressing, cock sucking adventure on tape or DVD. I'm going to leave you two girls alone for a few minutes to think it over, and you work Friday through Wednesday, your free time is your own, you can put a restrainer to hold your titties down, take off your make up and go live your normal life, or you are free to stay here." She turned abruptly and left the room.

"Sweet," Stevie said enthusiastically.

"Dude," I tried to reason, "we're guys."

"Guys who like to suck cock and dress up like women," Stevie insisted.

"I just found that out today," I said, "I'm not sure I want to become half woman, half man escort."

"Why not?" Stevie reasoned in his feminine voice, "it pays great, tax free, we'll do it for as long as we can, take our college courses on line."

I started to protest again, but everything he said made perfect sense. It was money for having sex, we enjoyed that, we enjoyed dressing up as women, why not be half women, see how the other half lives?

"Okay honey," I said in my fem voice, "let's do it."

"Hooray," Stevie smiled, we hugged each other, and went out to tell our new boss we would be glad to start right away.