tagTransgender & CrossdressersThe Right Girl for the Job

The Right Girl for the Job

byStephen_Heathcote©

"If you aren't here for sex, then why are you here?" Lacey asked. It was a reasonable question, given that we were sitting in the bar area of a brothel.

"I have some very specific fantasies, things that I would never ask a civilian to do," I said.

"Why not?"

"Too embarrassing. I don't even know if I can tell you," I said.

"There's nothing you can tell me that I haven't already heard," Lacey said. I liked her. Her face was kind and her body language welcoming. Sitting at that table she seemed more like a friend than a sex worker.

"I know I won't offend or shock you, but that doesn't make this any easier for me," I said. "This is stuff I've kept locked up for a long time."

"I know," Lacey said. "Take your time. Have some more water."

My hands shook so badly that the ice rattled in my water glass. I took a big gulp and set it back down. "I actually wrote all of this out last night because I knew I was going to be too embarrassed to say it," I said.

"Oh, cool. Let me see," she said.

"I threw it away." That made her laugh. I liked watching her laugh.

"Maybe just give me a hint," Lacey said.

"How tall are you?" I asked.

"Five-three. Why? Do you have something against short women?"

"No, no. I love short women," I said.

"I don't know how tall I am with my heels on."

"Let me see your foot," I said. She leaned back in her chair and placed her foot on my thigh. Her legs were smooth and muscular, her shoes a simple black leather pump. I stretched my finger the length of her sharp heel. "I'd guess you're about five-six with your shoes on," I said.

"That's pretty good," Lacey said. "So am I tall enough for you?"

"No, no. You're tall enough, but I don't know if your clothes are," I said.

She cocked her head slightly, like a dog hearing a distant whistle. "Is it a foot fetish? Some kind of giantess versus the tiny man thing?"

"No, nothing that complicated," I said. "I just don't know whether your clothes..." I took another big drink of water.

"Come on, just say it. If you can't say it here, where can you say it?"

"I just don't know whether your clothes will fit me," I said, and I stared at my water glass. I couldn't look at her.

"You want to wear my clothes? That's easy! I thought you had something really out there," she said. "We can do that."

"It's more than that. I want to be humiliated, called a sissy and a faggot and a cocksucker, told what to do, dressed up and made to parade around while you laugh at me, that kind of thing. Jesus Christ, I can't believe I'm admitting this."

"Did you see my profile online? I'm definitely the right girl for the job," Lacey said. She sat up straighter and looked me straight in the eye. If not for the fact that she was wearing a see-through dress, she may have been mistaken for a job candidate. "I'm really into fetish stuff, but I never get to do any of that around here. This is totally what I'm into."

"I need someone who is a creative talker, not just a cookie cutter dominatrix type," I said. "I'm not into bondage or pain or any of that stuff."

"I totally get it," she said. "You're a worthless little sissy faggot."

Adrenaline hit my bloodstream. My stomach flipped and my cock jumped in my pants. "That—that worked for me," I said. "Wow."

"And you've never done anything like this before?"

"No, I'd never ask a woman I was dating to go through something like this."

"Are you ready to make me happy, faggot? You're not getting another word for free," Lacey said.

"Yes," I answered.

"Finish your water and then come with me," she said. I gulped it down, and then she grabbed me by the hand and led me through a door at the back of the bar. We entered what looked almost like the lobby of a hotel, with big leather couches and animal heads hanging over the fireplace.

A display case filled with sex toys and souvenirs lined one wall. Scantily clad women walked here and there, clutching clients by their nervous hands. The clients tried to act suave, as if they were with dates rather than sex workers. Servers made their way through the lounge from the kitchen to the bar area. I wondered whether this all seemed strange to them or perfectly normal. After all, it was just another job running hamburgers and nachos from the kitchen to the tables except for the half naked women and the sex toy display. Over and over the door separating the bar and the lounge beeped as employees entered the security code.

Lacey pulled me by the hand past a little room similar to a doctor's office's reception area. An average looking middle-aged woman sat behind the sliding window. She wore a plain white blouse and blue jeans. "Room two, Sandy," Lacey said. The door for room two clicked and we stepped inside.

"Are you ready to do this?" Lacey asked.

"I think so."

"Are you going to do whatever I say?"

"Yes."

"What a good boy," she said. "You're such a good sissy. Now we just need to figure out payment." We negotiated, but she held all the cards. By that point I was a walking zombie. "Now drop your pants. I need to check your little dicklet. Oh, you are ready, aren't you? You're already dripping for me. Okay, pull them back up and follow me."

She took me by the hand again and we returned to the lounge area. As we made our way through the big room she said, "I think after I dress you up I'm going to bring you out here so that all the girls can laugh at you. How does that make you feel?"

"Terrified," I said.

"But turned on?" she asked.

"Yes."

"Good. Maybe I'll walk you around in the bar so that all of those real men can see you. They came here to fuck, not act like a faggot. What do you think they'll make of a sissy cocksucker in their bar?"

"It will probably piss them off," I said.

"They'll probably think you're disgusting," she said. "Yep, that's what we're going to do."

"Please don't make me do that," I said.

"We'll see." We walked down a long hallway and entered her bedroom. "I'm going to open the curtains so that I can get a good look at you in my clothes. Right now I want you to take a quick shower and get clean for me."

She walked to the bathroom and started the shower for me. When she leaned forward I got my first real look at her ass: round, tight, and muscular, flowing into firm thighs. I climbed into the shower and scrubbed like I'd just exited a radiation zone. I didn't want even the slightest scent of me to remain. I wanted to be something completely new. I wanted to be Lacey's sissy.

When I was done I toweled off and stood in her bedroom naked and awkward. I didn't know where to look or what to do. My erection jutted out in front of me, a bead of pre-cum glistening on its tip. Lacey rummaged through her dresser. "Have you ever worn a bra?" she asked.

"No."

"Well you're going to today." She handed me a lacey blue bra with huge cups. I had been so engrossed in my own little world that I hadn't realized how large her breasts were. "Go ahead, put it on. You know how, don't you?"

I wrapped the lingerie around my waist and tried to clasp it. "It's too small," I said.

"Well then you're just going to have to hold it up, aren't you? That's your problem, not mine. Now to find you some panties. Have you ever worn panties?"

"Yes," I said.

"When?"

"Often."

"Of course you have. That's what sissies wear, isn't it?" She handed me a small thong. "This should cover your little dicklet."

"That is not going to cover me," I said.

"Oh, well. Put it on anyway," she said. I pulled the strings over my thighs and between my ass cheeks. The little triangle of material couldn't even cover my testicles, much less my erection. "How do you look?" she asked.

"Ridiculous."

"Yes, you do. How do you feel?"

"Like I'm not even inside my body right now," I said.

"But good?"

"Yes."

"That's a good sissy. I don't like that bra. Let's find you something else," Lacey said. She moved to another drawer and pulled out a small, sheer dress, no bigger than a tank top. It was black with a couple of neon stripes across the front, like something a streetwalker might wear. "Should you be in this one, or should I take off the dress I'm wearing and make you wear it? Everybody would know it was my dress."

"I don't want the ability to choose," I said.

That made her laugh. "I wasn't asking you, I was thinking out loud," she said. She held out the streetwalker dress. "Put this one on. Not like that, step into it. Don't you know how to put on a dress?"

"No," I said.

"Well I'll help you. I don't want my little sissy to mess up my dress. There you go. That's a good boy. Now pull it down and cover your dick so that everybody knows you're wearing a dress. Oh, that looks so cute on you. Now we need stockings. Have you ever worn stockings?"

"No," I said.

She handed me a pair of sheer white stockings. "Put these on. How do they feel?"

"They feel good. Tingly," I said. They may have felt good, but they looked terrible. My leg hair curled and matted beneath the sheer fabric.

"I can still see your dicklet. Put these on," she said, and she handed me a pair of boy short panties. I stepped into them. "Turn around. Go on, spin for me," Lacey said. I turned around and she started to laugh. "Look at your ass in the mirror," she said. I turned my head. Across the back of the black boy shorts in big white letters was printed the word "slut."

"Are you thirsty? I know I get thirsty when I'm nervous," Lacey said.

"Yes."

"Then let's go get you some water." She opened the door and took my hand. We stepped into the empty hallway, Lacey and me in our sheer dresses, her breasts pressing against the stretchy fabric and my chest hair curling over the top of mine. "We're going to the kitchen. Are you ready?"

"No."

"But will you go?"

"Yes."

"What a good boy. I want everybody to see my sissy," she said. We began to walk. "Why are you looking at the floor? Hold your head up. Be proud of what a good sissy you are."

"Nobody could be proud of this," I said.

"That's true, but hold your head up anyway." I did as I was told. We passed a girl on the way to her room. She avoided my eyes. "Hi, Victoria, this is my sissy, William." Victoria kept walking. "How did that make you feel?" Lacey asked me.

"Terrible."

"But good?"

"Yes."

"Good."

The pattern repeated a couple of more times. "I'm so disgusting that they won't even look at me," I said.

"No, that's not it. We're told not to interact with each other's clients," Lacey said. "They're afraid they'll get into trouble. I know what I'll do."

We arrived at the reception window. "Hi, Sandy, I want you to meet my friend, William." Sandy looked perfectly normal behind the glass of her little business office in her jeans and her white blouse. She was thin, maybe fifty or so.

"Hello, William, I'm pleased to meet you," Sandy said.

"It's okay, you can laugh at him," Lacey said. Sandy looked embarrassed at first, but then she started laughing. "See you later," Lacey said, and she pulled me toward the kitchen.

We stopped at the tiled threshold. "Are you ready?" she asked me.

"Yes."

"Okay, let's go." I followed her onto the tile. The kitchen floor was cool beneath my stocking feet and my face burned with embarrassment. The kitchen staff looked up, looked a little disgusted, and went back to filling orders. "This is William. You can laugh at him," Lacey said. They didn't. We came to a cooler and she handed me a paper cup. "Go ahead, fill it up. Now drink it. What a good boy. Fill it up again." I did, and we left the kitchen.

We returned to the lounge. The door to the bar was just a few feet away. "Should we go in there so that everyone can see what a faggot looks like?" Lacey asked.

"Please don't make me do that. I can't do that," I said.

"We'll see," she said. "You want to make me happy, don't you?"

"Yes, I do, but I don't think I can do that," I said. Lacey smiled.

We headed back toward her room. She alternated between repeating "Hold your head up" to me and "This is William, you can laugh at him" to anyone we passed. Some did, most just looked annoyed. The annoyed look turned me on as much as the laughter did.

Back in her room, she asked me how our walk made me feel.

"I've never been so embarrassed," I said. "I can't describe how I feel."

"Like you've surrendered your dignity?" she suggested.

"Yes, exactly."

"What should we do now?" Lacey asked herself, and she looked around the room. "I know. I want to watch you pee."

"Okay," I said, and I stepped toward the bathroom.

"No. Right here. In your cup. Finish your water." I did what I was told, and then I flopped my erection over the top of Lacey's boy shorts and stuck it in the paper cup. "Have you ever peed in front of somebody before?"

"No."

"Are you going to be able to?"

"I'll try," I said.

We stood in silence for a moment. "Oh, there it comes. Good boy. Good sissy. Be careful, don't overfill it," she said. I stopped an inch before the rim of the cup that Lacey held. I looked directly at her. Her eyes were wide and slightly glazed, like the power drunk bullies I knew as a younger person.

She raised the cup to my lips. "Lick it," she said. I stuck my tongue into the cup and touched the contents. "More," Lacey said. She tipped the cup toward me and I lapped at it like a kitten. She tipped it further. "Drink," she demanded. I took a big swallow. "What a good little sissy faggot. You would do anything to make me happy, wouldn't you?"

"Yes," I said.

"I think I'm going to let you stroke a little bit." She sat on the edge of the bed. "Go ahead, jerk for me." I did as I was told. "Did you ever think you'd be standing in front of a woman, stroking your cock while you wear her clothes?"

"Absolutely not."

"How does it feel?"

"Amazing."

"I think you've earned a peek at my breasts. Do you want to see them?"

"Very much," I said.

Lacey smiled and let her dress's spaghetti straps fall from her shoulders, and then she lifted her heavy breasts. Her areolae were big and tan, her breasts large and firm. "Touch them," she ordered. "But don't stop stroking." We stayed like that for a couple of minutes, and then she announced: "Now I'm thirsty. Put your dicklet away. We're going on another walk."

We returned to the hallway. I don't know whether I was more comfortable in my new role or just so aroused that I didn't care anymore, but I didn't feel as self-conscious as I had on our earlier walk. We emerged into the big lounge. It was empty except for the traffic going to and from the bar, the girls and the wait staff repeatedly opening the heavy door with the beep beep beep of their security codes.

I stepped toward the kitchen, toward Sandy and her reception window, and Lacey pulled on my hand. "No, that's too far. I'm thirsty right now. This is closer," she said, and she walked toward the bar door.

"I can't do that," I said. "Please don't make me do that."

"Come on, just walk to the door with me," she said. We stood near the door. Waiters and girls said "excuse me" as they made their way past us. Lacey didn't say anything, and neither did I.

Eventually she caught the door as it swung open and held it. That thick piece of wood was all that separated reality and fantasy. On the other side of the threshold the music was loud. People crowded around bar tables eating, drinking, talking, laughing. On our side of the threshold I was dressed like a cheap hooker and a bitter taste lingered in my mouth. My fully erect penis pressed against the thin fabrics. There was no hiding it.

"We're going in now," Lacey said.

"I can't. It's too much."

"Yes you can. You want to make me happy, don't you?"

"Yes."

"And you'll do anything for me?"

"Yes."

"Anything?"

"I can't do this," I said.

"Are you going to cry?"

"I might."

She lowered her voice to a soothing, calm tone. "Just put one foot across. There you go. Now put your other foot across. There, you did it. Who is looking at you?"

I surveyed the room. Life went on as if nothing momentous had just happened. "Nobody," I said.

"Then let's go get me a drink," she said. We only had to take maybe five steps to get to the bar. Several of the girls sat on bar stools nearby, nursing drinks and talking to each other. "I want you to stand right here for me, okay?"

"Can I turn and face the wall, please?"

"No, you face the room so that everybody can see what a sissy looks like," Lacey said. I crossed my arms across my chest, as if that would somehow make me invisible. "And hold your head up. Be proud of what a good faggot you are."

First the girls started murmuring. One whispered into Lacey's ear. Another approached me and said to Lacey," I want to meet your friend."

"This is William. It's okay to laugh at him," Lacey said.

"Hi, I'm her best friend," the woman said.

"Hi," I said. I didn't know what else to say. People in the bar were looking now. Some laughed, some leaned to whisper to each other, others looked away as if nothing unusual was happening. A couple of customers looked genuinely disgusted. Lacey ducked behind the bar and filled a water glass, and then she led me back through the door, back to safety.

"How did that feel?" she asked.

"That was the most humiliating thing that has ever happened to me," I said.

"But you liked it, didn't you?"

"Yes, I did."

"Did you see Brandy whispering in my ear? She asked if I had you locked up in chastity. That's a good idea, don't you think?" I couldn't think. I'd left my body five minutes ago.

When we returned to her room, she handed me my cup and made a toast. "To you being such a good sissy," she said, and we both took a swallow. I tried not to gag. "I think you've earned yourself a smother session. Go lay down on the bed."

This was too much to hope for. Lacey straddled my chest and lifted her dress. I caught a glimpse of her silky white panties, and then her ass dropped onto my face. I couldn't see. I couldn't breathe. I was in heaven. I withstood it as long as I could, and then I tapped on her thigh. She rose up and I gasped for air.

"What's the matter, can't you breathe? Breathing is for men, not sissies," she said, and she dropped her ass onto my face again. I jerked my cock while I struggled for air. She didn't stop me, so I guess it was okay.

When she lifted up again, she asked how many people saw me in the bar.

"Twenty or thirty," I said.

"What do you think they thought?"

"That I wasn't a man," I said.

"That's right. A man wouldn't wear my panties and stockings. A man would fuck me." She smothered me with her ass again. Over and over she took me right to the edge before letting me gasp in a little fresh air, all the while repeating what a worthless faggot I was.

Eventually she tired of this game, so she dismounted me and ordered me to stand up. "Take off my boy shorts but leave my thong on. Turn around and bend over. That's a good boy. Is this my ass?" she said, and she slapped my bottom.

"Yes," I said.

"Spread it for me." I reached behind and spread my cheeks. "Look at the little hole opening and closing. You want me to fuck it, don't you?"

"Yes."

"Say it."

"I want you to fuck it."

"Say it louder."

"I want you to fuck my ass."

"I want them to hear you in the next room."

"I want you to fuck my ass," I said louder.

"Tell me you want me to break your ass."

"I want you to break my ass."

"What are you?"

"I'm your sissy faggot cocksucker, and I want you to break my ass."

"Louder."

I yelled it again, my hands holding my ass wide. I didn't realize until then that I was rocking back and forth. Lacey reached between my legs and stroked my cock.

"You will do anything to make me happy, won't you?"

"Yes, anything."

"You'll take it in all your holes."

"Anything." My cock was purple and dripping.

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byStephen_Heathcote© 7 comments/ 20142 views/ 16 favorites

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