I came through arrivals with just the small carry-on I packed for after the weekend – a change of male clothes for the flight home, similar to what I wore for the short flight to my destination: socks, a matching set of gray sweatpants and baggy hoody. The only girly thing I had in the bag and that I wore on the flight were simple black lace panties. Once I came through customs, I put on the hoody and a pair of Ray-Bans to discretely conceal my clean-shaven face. I was that worried about being recognized, though I didn’t know anyone in this small city. A moment after I assembled my simple guise, I saw a middle-aged black man with a placard bearing the name I requested on the online form: Jolene.

My heart thumped. That was me. My only name for the weekend. No one would guess looking at me now. I walked toward the man with the sign but not to him, still afraid of what I was about to do, still deciding to go through with it – walking as though I could continue past him, pretending it had nothing to do with me. Probably he’d seen this act before, because right at the moment I could have kept going and gave up the whole plan, the man turned and walked in step with me and asked, “Is this you? I have the car right out front. We’re all set to go now?”

His tone was so disarming – like our business there at the airport was mundane, not scandalous; drivers pick up all kinds of people every day and think nothing of it. He gently put his hand on my back and ushered me in the direction of the exit doors. “Right this way.”

In the back of the black Lexus town car, there was a small gift bag with a tag on the handle: For Jolene. Inside: a small bottle of red wine, a jeweled plug, a small tube of lube, a couple of sanitary wipes, and a note:

Dear Jolene,

We wish you a warm welcome to SissyDreams. We hope your travels have been uneventful and you’re relaxed and ready for the weekend – but in case you’re not, here’s a small bottle of wine on us. :) You’ll notice another gift in the bag just for you. This is also to help loosen you up, hehe, for the weekend to come. If you’ve followed our intake instructions and cleaned out before your flight, we recommend inserting it on the way over. You will be thankful later when your program begins.

Love,

The SissyDream Team

PS –Malcom, your driver, is ready to assist you with any help you might need on the way from the airport.

We were on the highway now. I looked at Malcom in the rearview mirror.

He caught my eye, reached over to the passenger seat and held up a clean wine glass. “Will you be having that drink?”

I accepted the glass from him and gave a timid thanks. I needed the drink badly. And I knew when I was finished I would proceed to the next step of the instructions. I was to put my new butt plug in, right there in the car.

The wine was gone too quickly. I had the plug on lap, nestled in the wipe I polished it with and I took the lube capsule out of its plastic package. The capsule had a tear line for opening it, but I couldn’t quite tear it with my hands, like it had not been serrated correctly. Defective. I struggled with it for a minute before Malcom spoke up.

“Having trouble back there?”

“Ha, yes, I can’t seem to open this.”

“Yeah those can be tricky. Pass it up here.” He held his hand up for it. His hands were big, his fingers thick. I didn’t see how he was going to do any better than I could.

“Listen,” he said, “once I open this, you gotta put the open end in your hole and squeeze the lube in, then you grab that plug and it should go right in. Ok? So before I open it, you should be ready for it.”

“Ok.” My heart was racing.

“Go on and pull your drawers down. Better take one leg out and prop your feet on the back of front seats. I pass this to you, stick it in, then you work that plug in. That’s the best way, you hear me?"

“Ok.”

“Alright, you got this.  Now get your ass up and ready for it.”

I felt like I was in a trance following his instructions. There was nothing more to say. He’d clearly commanded me and I was following through. My sweats and panties were down; I took one leg out and I propped my feet on the backs of the front seats.

Malcom watched in the rearview mirror.  “Damn, that’s a tight ass.” He put the capsule in his mouth, tore the top off with his teeth and reached back to hand it to me. I took the tube, inserted it and squeezed. Then I grabbed the plug and circled it around my hole, coating it in the dribble of lube that leaked out, and Malcom was glancing back the whole time, mmm hmms escaping from his throat. “You got it girl, now put it in.”

The plug slid inside me and a moan escaped my lips.

“There you go,” Malcom said. “See, easy. Now pull it in and out a little, make sure it gets all lubed up.”

“Ok.”

“Nah, girl you’re almost at the location. Won’t be but ten minutes now. You better get comfortable with this, all right? You can say 'yes' like you mean it.”

“Yes.”

“Good girl. Now let me see you move it. Go on, in and out.”

“Yes, Daddy.”

“Oh, damn! Now you got it. Keep it nice and slow.”

I slowly worked the plug in and out, and Malcom kept his attention divided between the road and me. By his movements I could guess he’d taken his cock out and was stroking it, or maybe he was rubbing himself through his pants – I couldn’t see – but I kept playing with my plug with both my pleasure and his enjoyment on my mind. The plug was now hitting my spot. A pleasurable ache was building and if I wanted to I could bring myself to a sissy-gasm. I changed my pace, kept myself on the edge, and I realized we had turned off the highway and were in an industrial part of the city, then on a narrow backroad with lot after lot of what looked like warehouses. There were trucks around with drivers high up in their cabs on the side of the road and I was afraid they could see what I was doing.

“All right,” Malcom said. “You’re all good now. Go ahead and get dressed. We’re almost there.”

“It’s in this area?” I said, incredulity creeping into my voice. It was beyond shady.

“Don’t worry, girl. It’s all good. Nothing bad’s gonna happen to you that you don’t want to happen, you hear me? It’s all good. You trust me?”

“I don’t know. I don’t like the way this looks.”

“Nah, Jolene. What we did back there, you wanted all of that, yeah?”

“Ok, I did.”

“Come on, Jolene, we can do better. Yes what?”

“Yes, Daddy.”

“Yeah, there’s my girl. You’re gonna be all right. I promise that, deal?”

“Yes, Daddy.”

“Good girl. Here we are up on the left."

We pulled into a gated asphalt expanse with a big box-like warehouse planted in the middle. Next door, at another warehouse-like building, came the sounds of metal work – perhaps it was a metal fabrication factory. Who knows what went on in these building on the outskirts. If they saw me getting out of the black Lexus, Malcom leading me by the hand to this unmarked location of SissyDreams, they would probably wonder the same thing: What exactly went on in there?

“You go inside,” Malcom said. “Up the stairs to the room on the left. They’re waiting for you.”

“Thank you, Daddy,” I said. As I stepped into the dimly lit warehouse, he tapped my ass on the plug and shut the door behind me.