Sissyboy jake's first outing – part 1

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Thank you for your comments. I left off telling the story just around 12:30 in the afternoon. Karl and Rashid had just had their way with me in the basement.

I lay on the thin blue pad, exhausted and somewhat dazed. As I said, I am very new at this and didn't expect such harsh treatment so quickly. My bottom was sore and I actually thought I felt my insides twitching. My legs were shaking. I felt the warm fluid trickling out and down the back of my leg, pooling on the pad underneath me. This was my first time and they had been so rough. If Tiffany hadn't prepared me so well, I doubt I could have survived it.

Karl and Rashid were both getting dressed. Karl was laughing and talking with Rashid about how nice and tight my ass felt, how I compared to the last few sissy-boys he'd brought down here. It was awful, hearing them talk about me like I wasn't there. As if I did this all the time and this was just another trick.

"She's tight, I'll grant you that, but she doesn't show much enthusiasm," Rashid complained.

"Remember, my friend, she is new at this. Tiffany told us she might even be a virgin," Karl said.

Rashid stepped forward and nudged me with the toe of his shoe.

"Is that right, little whore? Did we take your cherry?"

I didn't answer. Couldn't answer. They had, and they had been completely callous about it. I wanted to call the whole thing off right then. It wasn't what I'd imagined, not at all.

"I asked you a question," Rashid said. He crouched down behind me and I felt something pressing against my bottom. I wanted to jump to my feet but I was too sore. I straightened my legs and pushed myself up on one hip. Whatever it was, he was sliding it idly up and down along the underside of my balls.

"Yes, Sir, you did," I said. My voice was a whisper from far away.

Karl leaned close to me and tipped my head back, his hand under my chin. "I didn't hear that," he said.

"Yes, Sir, you are . . . you took my ass cherry." I choked on the words, I'd never thought of it that way and I wasn't sure how I felt about it. But I knew that I hated saying it.

"Get up," Rashid said

I pushed myself to my feet, feeling the warm cum drizzle down my legs as I stood straight. I smoothed out my corset. One of my stockings had come free of its garter clip, so I bent down and reconnected it. Another gush came out of me. This time it made a little bubbling sound and I turned bright red.

"You're dripping," Karl said. He threw me a pair of men's briefs. "Put those on." I did.

Rashid and Karl motioned for me to follow them. I picked up my dress and shoes and carried them with me. We went through the basement and up the stairs. They led me up a flight of stairs, then down a long hallway and finally into the bedroom.

The room was very modern, chrome and glass tables, aluminum dresser and chest. The carpet was light eggshell, almost white. One wall had an outdoor window and the two adjoining walls were mirrored closets from end to end. The bed had a simple metal frame all the way around and no headboard. There were pictures on the walls, large black and white lithographs of torsos. They were cropped such that you couldn't tell which were male and which were female.

On the bed, I saw a classic French Maid outfit. Tiny, black satin corset dress with a frilly white apron. Black stockings and high heels, a silly looking hat and a feather duster.

Rashid left and Karl motioned toward the bed. I sat down on the edge, my knees together, my dress and shoes in my lap.

"Once you're put on the outfit, make the bed and tidy up this room. There's laundry in a hamper in the closet, the machine is downstairs, near where we took you earlier. You'll find hampers in each of the rooms. Four on this floor, four upstairs. Do as many loads as it takes.

"While the machines are running, you can come back upstairs and make the beds. These rooms were all occupied last night, so they all need to be checked. You don't need to change the sheets unless you see a reason." He turned toward me.

"Are you getting all of this?" he asked.

I was, but I didn't know what to say. It didn't make any sense. Tiffany had dropped me off here for them to use and they were having me do the laundry? I squirmed, feeing the dampness where I was leaking into the underpants. My balls were sticky from the goo. Thinking about it made my cock start to stiffen.

"Hey, Sally! Are you getting all of this?"

I nodded. I was, even though it made no sense. I was getting it. Karl evidently understood the look on my face because he just smiled.

"All right, then. Come and find me when you're finished with all of that and I'll have your next assignment. By the way, when you put on the outfit, you don't need to tape yourself. Let it all hang out. We don't really care that much. You're here to work, not to look pretty."

Karl left me alone with the outfit and the clothes hamper. I wanted to shower and get some of the gunk off of me, fix my hair and makeup, but my months with Tiffany had taught me to not do too much thinking for myself. They hadn't told me to shower so I wasn't going to shower.

I took off my outfit and folded it neatly on the bed. I caught a look at myself in the parallel mirrors. My body was reflected infinitely down each wall. There was something hypnotic about it. I stared for two full minutes before I realized my focus was on my backside, on a spot that had dried about six inches down the inside of my right thigh. I felt embarrassed and looked away.

I put the outfit on quickly. Tiffany must have given them my size because it was perfect – the corset snug, the stockings high and the skirt just at the bottom of my arse. I turned to look for the laundry hamper and saw myself in the hall of mirrors again. A French Maid, indistinguishable from a thousand other French Maids dressing up in costumes to please boyfriends, husbands, and lovers. Or, in my case, complete strangers into whose hands my lover had delivered me.

The clothes hamper had only a few things in it. I carried them in one arm and went down the hall to the next room. It was completely different, it looked like a 1950's bedroom, the clunky bedframe, the ugly lamp. The hamper was half full so I put the other clothes in and carried it with me.

The other two rooms were decorated in themes as well – a Parisian brothel and an Old West Honky Tonk. The hamper was full now, I'd need to come back and do another load. As I went down the stairs to the first floor, I saw a couple walking toward me. The girl was looking at me and giggling. She pressed her head against the man's shoulder. The man laughed and pulled her close.

"It's one'a them sissy boys. I heard they do the women's work around here," he laughed. He held up his hand and I stopped a few feet in front of him. "You doin' the laundry, Nancy?"

I lowered my eyes and muttered, "yes". He laughed and they walked by me. I jumped when he smacked my ass. The girl giggled again.

I walked down the stairs, feeling dizzy and confused. Why was this turning me on? I was doing housework, the menial task of putting dirty clothes into a washing machine, and it was turning me on. I measured the soap, turned on the water, and set the timer. The machine started up. I felt the vibration under my palm and had a flash of an image of me pressed up against it, feeling it against me like a huge steel vibrator.

While the machine filled, I went back upstairs. I made the beds in the first two rooms. The feel of the cool sheets under my hand as I smoothed them aroused me. The glimpses I caught of myself in the mirror aroused me. The smell of the sweaty underclothes in the hamper aroused me. It was so confusing. I wondered what I might be turning into.

The third room was occupied so I went and collected the hamper from the fourth one. On my way down the stairs, I passed another couple. As they went by, the woman slid her hand up my right thigh. I froze.

"Randy, you were right," she said. "She's a man." She slid her hand all the way until my limp dick was in her hand. "Well, she's got a prick anyway."

Randy sneered at me.

"That ain't no man! And I'm not paying for you to tease the help!" he barked. He grabbed her arm. She gave my balls a hard smack and I crouched, pain shooting up into my gut. They vanished up the stairs and into the room I'd just cleaned.

I leaned against the stair rail for a minute to catch my breath. Tiffany could be harsh but she knew how much I could take. This girl didn't know me from Adam and had really slammed them.

When I could gather my thoughts, I continued down the stairs. I thought about what he said to her, about the different themed rooms, about the room in the basement. They were running a brothel!

Why did it surprise me? What did I think? They just had a weird decorating scheme? I set the hamper in front of the washing machine and looked around. Everything looked so normal. Shelves with detergent and boxes of light bulbs, stacks of towels and toilet paper, just another household. But it wasn't. It wasn't at all.

When I got back upstairs, the first couple was already coming down.

"Get me something to drink," the man said to me. I stared at him for a second.

"Are you deaf?" he growled.

The girl next to him, a tall, dark haired hooker who looked to be in her middle twenties, gave him a kiss and said, "I think she's new."

She pulled me gently down the hallway and into the kitchen. She led me to a stool and I sat down. She went to the cupboard and opened it, took out two glasses.

"First time?" she asked.

I stared at her, lost, and nodded.

"Who brought you here?"

"My Goddess, the Mistress Ti…"

She held up her hand and laughed. "Don't. You don't need to play that and "slave' shit with me. Girlfriend? Boyfriend? Wife? What?"

She opened the refrigerator and took out a big pitcher of lemonade, poured the two glasses half full. She filled the rest with ice.

"Girlfriend. Lover. Something like that," I said, trying to relax. She was friendly but I was on my guard. "She's training me."

"Duh!" she laughed. She handed me one of the glasses.

"Drink up," she said. "Then get back to work before they notice."

"Before who notices?" said a voice. Rashid.

The girl spun and saw him standing in the doorway, arms crossed, listening.

"I…" she started.

"Shut up." Rashid took the glass from my hand and waved me off. "Go do your />
As I walked to the door, I heard him yelling at her. "Two years. Two years, we've been together. You've made how much money? I take ten percent for rent! That's it! Why do you have to keep sticking your nose in where it doesn't belong?"

"I know, I know, what can I say? I'm a soft touch."

Rashid calmed down and laughed. "I know, I know. I shouldn't have let you book today. This one is in training." That was all I could make out as I walked farther down the hall.

This must have been the place Tiffany told me about. A friend started it years ago. It was a place for bored housewives and ambitious girls to pick up some money. I hadn't made the connection because of Rashid, but Karl must have been the same Karl she'd told me about.

For the next two hours, I did nothing but housework. It was tedious and I was teased by some of the hookers, but mostly it was just boring.

At two-thirty, Rashid introduced me to something new. He led me out the back door and across the yard to a garage or toolshed.

"At three, you will be entertaining a small group of clients." He picked a bit of lint off the front of my dress. "There will be four of them." He brushed back a strand of my hair and put it over my left ear. "You'll be all right. Shhh."

I was anxious and nervous. This man had been so brutal last night and now, he was talking gently, quietly, almost trying to reassure me. He brushed my hair again, running his fingers through the dirty strands. I felt embarrassed and nasty, too dirty for him to touch.

"There is a box in the room, a Glory Hole box." He slid a hand down my side and rested it on my left thigh.

"You'll be on your knees. They only want to use your mouth." He closed his hand around my cock. I felt it start to stiffen. My fear of the man wasn't enough to prevent my body from responding. I thought for an insane second about the idiot who said raped women couldn't get pregnant. Bodies can't always defend themselves.

He leaned in close and pressed his mouth against mine. I was shocked but responded easily. My cock stiffened fully now. I felt his warm tongue inside my mouth, probing and insistent. My knees went weak and I reached behind him, pulling his face close to mine.

"Clap! Clap! Clap!" The noise from behind me made me freeze. At least two pair of hands clapping. Rashid jerked his head back and spit in my face.

He spit again, this time it landed on my lip.

I turned around. Four huge college-aged men in khakis and tight shirts were staring at me and laughing.

"Every bit the pig Karl said he'd be," one of them laughed.

"Yeah, come on, Rashid, let's get this show on the road," one of the others – the black one – said. They circled around me and led me into the building.

The Glory Box was about three feet across and had two holes in each side and one on each end. They pushed me into it and slammed the door. I had to kneel because the roof was too low to stand. My bottom was pressed against one wall and my face just a few inches from the other. I heard a padlock click.

They talked and laughed for a while but soon enough, the first cock came through the hole. It was thin, pale and limp, like a scared little animal of some sort. I kissed it tentatively. This was different from the throat fucking I'd had last night, now I had to be an active participant. I kissed it and heard the man outside laugh.

"She thinks she's my girlfriend!" he said. "Come on, honey! You know why you're down there!" His words turned me on and I felt myself getting stiff. I opened my mouth and took the head between my lips, sucking gently, my tongue licking the underside of the rim. He was hard in just a second and started humping against the box. I tried to relax my throat like Tiffany'd taught me but his timing was jerky and crazy.

Something stabbed at my shoulder. Then something else pressed against the outside of my right leg. I slid my arms around until I could take both of the new cocks in my hands and stroke them. The men outside were laughing now and talking about pictures. As they described them, I could tell they were looking at lingerie photos Tiffany had taken of me!

"Nice thighs."

"Look at those ass cheeks."

"She's taking that whole thing up her arse."

They were either complimenting or insulting me, I wasn't sure from their tone of voice. It didn't matter though, my focus was on the cock that kept sliding in and out of my mouth with random, unpredictable abandon. I kept trying to circle the head with my tongue to get him to cum but he just kept hammering away at my face. The cocks in my hand were only mostly-stiff, I could tell they were waiting for their turn at my warm mouth.

The first cock started cumming and I gulped down as much of it as I could. I heard him go wild as I swallowed, the pulse of my throat pulling his cock head further into me. He pulled out before he was finished and I felt a stream of warm goo shoot up my nose and all over my cheeks and lips. As much as I wanted not to, I couldn't resist licking myself clean. The sweet, salty taste made me gag, I wondered if I'd ever get used to it.

The second cock came fairly quickly. While the third one was assaulting my face, I felt someone sliding his finger up and down my ass crack through the back hole. Three of the four voices gathered back there and started taking bets on how many fingers they could push up into my bottom.

I lost focus and gagged on the cock in my mouth, coughing and sputtering for a few minutes until I got the rhythm back. The man fucking me didn't even slow down.

When I was quiet again, I felt someone's wet finger pressing against my bung. My insides went soft and I felt my knees open and my arse relax. It was horribly humiliating — I was readying myself for it! I was eager for it!

The tip of his finger was just past the tight ring when I heard Rashid's voice. "No free samples! You want her pussy, you pay!"

They broke out in laughter.

"Her pussy!"

I felt the cock in my mouth soften and then it was gone. A few minutes later, the padlock clicked and Rashid opened the box. Karl and Rashid helped me to my feet.

"You did well," he said. I wiped the back of my hand across the cum that was dripping down my face. Then I realized there was nowhere to wipe my hand.

"You're free until four Karl said. I looked at the wall clock. Three-fifty.

"May I use the bathroom? And brush my teeth?" I asked. I wanted to get the taste out of my mouth and I needed to pee.

"No. It isn't time for your toilet yet," Karl said without any explanation.

"May I at least brush my teeth?" I asked.

"No point," Rashid said with a smile. "No reason."

Karl smiled at me and said, "yeah. Whores like you don't kiss on the mouth, />
— end of part 2

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Tags: fiction anal transvestite humiliation domination/submission oral sex sex story


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