sissyboy jake’s first outing – part 1_(0)
sissyboy jake’s first outing – part 1_(0)
| Sex Story Author: | culotte.de.dentelle |
| Sex Story Excerpt: | Thinking about it made my cock start to stiffen. "Hey, Sally! Are you getting all of this?" I |
| Sex Story Category: | Anal |
| Sex Story Tags: | Anal, Domination/submission, Fiction, Humiliation, Oral Sex, Transvestite |
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.
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