How Did He Know? Pt. 03

I woke up with images of last night flashing like a strobe light in my brain, with an accompanying audio...the voice of Marcus and his haunting words "Your world changes tomorrow." I'm trying to process everything I said and did last night and I'm struggling to reconcile it all.

I like to wear panties and a butt plug and hide it from everyone. Sure, part of the thrill is the remote possibility that I'm discovered. But how the hell did some random black dude know? And how did he know about my secret obsession with big black cocks? I thought I could always repress my fantasies deep enough that they would never bubble up to the awkward surface.

But the first time I see a real black cock, I turn into a little bitch boy?

Ok, it WAS a magnificent cock and it got as hard as steel. I mean my cock gets hard, but not that hard. And what the fuck did I smoke? It wasn't hash for sure. I've never been so horny in my life. That shit changed me.

How does he know my number and where I live? I've never seen him before. And what am I going to do about tonight?!?

I zombie through half a day of work a half thinking up a plan to get out of this. Well, kinda.

Marcus and Keith want to tag team me tonight. They both have huge cocks and they are going to do whatever they want to me so I have to weigh the possibility of getting injured and an embarrassing ER visit...against an incredible opportunity to live out a huge fantasy of mine. I've only had modest sized toys in my ass and I've never really "pounded" myself either.

I've decided to go with them under a few conditions. First, they have to go slow. I mean nobody is going to have a good time if I'm choking and throwing up at one end and bleeding from the other. Second, we'll have a safe word. Third, they have to wear condoms and finally, I am not doing any drugs. Whatever it was, it made me lose all inhibitions and I want to remember my first, and maybe only, experience. If they don't agree, I'll take an Uber back home.

At 7pm, I've cleaned out and up, have all my girl stuff in a small duffel bag and I'm dressed in guy clothes...with white cheeky panties and a small butt plug.

My phone dings and it's a text from Marcus.

"Your ride is downstairs, sissy."

"Yessir"

Outside there's a black Lexus with dark tint so I can't see Marcus, but he sees me with the bag and he pops the trunk. I get in the passenger side and it's not Marcus who's driving.

"Well you're not the usual type," says a well-dressed black woman. "I'm Trish and you're Jamie."

"Yes, good to meet you. Where's Marcus?"

"I work for him and I'm going to help you get ready for tonight. We have to make one stop before we get to the room. We have to get you some slutty makeup, sissy." She giggles a little and looks over at me. "How old are you, darlin?"

"Fifty two"

"Damn. What in the world is he doing?" She said with her voice drifting off at the end. I didn't think she really wanted an answer so I sat quietly.

After about 10 minutes we were heading into a rough part of the city. She pulls into a Family Dollar parking lot and we're soon walking through the front door. It, and all the windows were thick plexiglass protected by steel bars.

I follow Trish over to the makeup section and she moves me into the light and holds up a few different shades of foundation to my face. "Pick out a red lipstick and then go match it to a nail polish. You need a really slutty red, sissy," she says loud enough to hear two aisles away!

I look down at the floor and walk over to the lipstick. As I am leaning in to get a better look, I hear someone say "over there" and see two black teens pointing at me from down the aisle. How embarrassing. I pick two lipsticks and look for the nail polish. Trish tells me it's one aisle over and when I find it, the two black kids are there, smiling.

"Need some help, faggot?"

"You gonna get that black pipe tonight, sissy?"

"Get the fuck outta my way." I say as Trish rounds the corner. "Move along fellas. Don't hurt her, Marcus got big plans for this one."

"Marcus? Fer real?"

"Aight then"

She takes the lipstick and nail polish from me and says, " Nah nah. We're gonna go with pink. Neon pink for you. Marcus loves to see all that pink around his big cock." Again, loud enough for most of the store to hear.

She makes me pay for everything and her and the cashier had a few laughs at my expense. We get back in the Lexus and five minutes later we pull into the lot of a small motel. It looks like a Section 8 motel that needs some attention. She parks in front of the unit on the end and uses a keycard to open the door.

Trish: "Marcus has an arrangement with the owner. This is his suite."

It was like we walked through a twilight zone door. We entered into a big living room and then the huge master bedroom with a bed that was bigger than a king bed and a big bathroom with a well-lit vanity.

Trish walked toward the small kitchen and told me to unpack my bag on the bed so she could see what all I had. I put everything neatly separated on the bed as she walked in and handed me an open bottle of grape Gatorade.

"You're in for a long night so you need to stay hydrated. Sip this one slowly."

It has a metallic taste to it and I look at the purple liquid. "Don't worry. I added something to help with your nerves."

She quickly goes through my collection of panties, lingerie and the few outfits I have and tells me to get the duffel bag.

"None of this works. Put it all back in the bag and go take a shower and take the lotion on the sink and put it on everywhere. Then we'll get you dressed."

I had already shaved my body this afternoon so when I get in the shower, I'm running my hands over my smooth legs and butt. Whatever was in that Gatorade was making me squeeze my ass cheeks hard, imagining it was Marcus.

Fuck. I said I wasn't going to do any drugs and I'm drinking this Gatorade that I know has something in it. Trish said it would help my nerves, and it has, I feel loose...and very horny. When I'm usually horny my cock is hard but right now, I'm putting lotion on my body and I'm going really slowly over my ass, my cock and my balls and when my finger stops and circles my hole, precum drips from my limp cock.

Trish's voice snaps me out of my mini trance, "You ready in there? Open up, we've got a lot to do before the boys get here."

I grab the robe that's hanging on the back of the door, put it on and open the door. "Pink favors you, Jamie," Trish says as she walks to the first vanity and places a large bag on the counter. I look in the mirror and the robe is powder pink satin that stops right above my knees. I look, and feel, very feminine.

Trish is sorting through everything and she hands me a package of fake finger nails. "Here, you get started on these while I pick out your shades."

The nails are the press-on type. I find them very easy to apply and I have them on in under 20 minutes. Trish has turned me away from the mirror so I can't see the progress she has made. I've been sipping the Gatorade and I feel hypersensitive and increasingly sensual with everything that's happening. I love my new French nails and Trish has me smelling different perfumes. "I like this one," I tell her and hold a bottle up.

"Good, that's Marcus's favorite." When she said it, I felt a rush of blood go to my face like I was blushing. She notices it too and asks if I'm alright.

"Yes, I don't know what was in that drink but yeah, I'm feeling different."

"I'll get you some more."

"No! I mean I can't do anything more. He made me smoke some stuff last night and it changed me so that's one of my conditions for tonight...I'm not going to any drugs."

"OK. You don't have to do anything you don't want to do, sweetie. You said one of your conditions?"

"Yeah. I also need them to go slow. I'm very inexperienced and I'm still a virgin so I don't want to be choking or get my ass torn up my first time. So we'll need a safe word too."

"OK, OK, I can see that. You're going to have to tell them this when they get here. Anything else?"

"Yeah. I know black guys don't like to wear condoms but that's a dealbreaker for me. Maybe after I know them better it'll change, but until I'm sure that everyone is clean, we use condoms. I know I'm clean."

"Well, Marcus and Keith are clean but I feel ya. Just gotta let them know."

Trish is putting the finishing touches on my makeup and my blonde wig with pink streaks and I ask if I can see myself yet but she says I have to wait until I'm dressed in my sexy lingerie first.

We go into the bedroom and she has everything laid out on the huge bed.

"Start with the stockings and belt," Trish says. She is referring to white fishnet thigh highs with a matching garter belt. It's the first time I've worn these and Trish helps me put them on. I'm really wanting a mirror and I ask Trish if I can get something out of my bag. She's onto me and tells me she'll bring it out of the bathroom. I run my hands with my new French nails up and down my stocking legs and I'm really starting to feel submissive...and horny.

She drops the bag at my feet and I immediately zip open a pocket, reach into a bag and pull out a decent size butt plug. "Yeah, you starting to feel it now, ain't you sissy? Go ahead, you'll be glad you did. You ever take a cock as big as Marcus's?"

Right when she asks the question, I push the plug all the way in with one motion. I moan loudly, sounding just like a woman, catch my breath and say, "No, I'm still a virgin."

I look up and see Trish staring at me with a slight smile on her face. "Well good for you, Jamie. I'm sure you've thought about this night for a long time. Are you feeling more like a woman now?" I nod with my eyes closed, listening to her sexy voice, wiggling my butt around the bed, playing with my cock with the precum that leaked out when I put the plug in. I feel her close to me and I feel her slip something over my head and feel a very soft and smooth blindfold on my face. She's almost whispering when she says, "its ok, girl. You're doing good and it will be everything you dreamed about, Jamie. Keep your eyes closed and dream away. Just follow what I'm doing and we'll get you all ready."

"Thank you, Trish. I know you don't really want to do this so I appreciate it."

From across the room I hear her say, "Why do you say that, Jamie? I do this for Marcus at least once a month and its mostly the same...but you're different. I don't know what he has in mind for you but he's smart as a motherfucker so I trust him. And if there's one person in this world who can fuck you and make you feel like a woman...its Marcus"

I moan again and say in a sexy voice, "I know. That big beautiful cock..."

She tells me to stand up and when I do, she grabs my cock and balls with one hand and holds onto my shoulder with the other to steady me. Then she whispers in my ear, "You're going to be such a pretty girl, Jamie. Pretty in pink. Marcus is going to turn you into a woman, baby. You'll never want to have sex again any other way, but as a woman. So I'm going to lock this up. Your pleasure won't come from here anymore. He's going to give you a pussy tonight, girl."

I am out of my mind with pure lust. She has put me in some kind of chastity device that feels snug but not uncomfortably so. In my ear, "Don't worry. It's pink too and you look so sexy, girl." I'm fucking loving her calling me girl. Instead of trying to feel my new device, I reach around to play with my plug. "That's it, Jamie. Focus on your pussy like a good girl. Do you need a bigger plug yet?"

"Yes, please," I answer quickly and we both laugh which breaks up the trance I was slipping into. She has me kneel on the ottoman at the foot of the bed and then gently pushes me down on all fours. I feel her pull out my plug very slowly and when it's completely out, I drop down my shoulders automatically and picture myself in a whorish face down-ass up pose. "Mmmm, look at you, you're a natural. You sure you're a virgin, girl?" I think back to when Marcus said I was a natural and it makes me think of his glorious cock. "This one is bigger so I want you to slowly inhale through your nose when I tell you too and-"

"No no," I cut her off. "I'm not going to do any of that stuff he made me smoke last night."

"It's not that stuff. You ever do poppers before? They'll help your pussy loosen up for this plug. That's all," Trish says in that sultry voice. "Trust me, Jamie. I'm going to be with you the entire time." I do trust her. I've heard of poppers but never tried. They sell them OTC so how bad can they be? I start to slowly inhale until she tells me to stop and hold, then exhale when she says and do it again with the other nostril.

About 20 seconds later, I feel a rush of warmth wash over my entire body and hear Trish say softly, "You feelin alright, baby?" I just arch my back more and moan loudly. Then I feel her pushing something big into me and stop once it's in a couple of inches. My God that feels so good, I feel myself starting to push back against it first slightly and then in one thrust, the entire plug is in me and I'm still pushing back harder.

"Perfect, Jamie. You look so pretty right now," Trish says as she squeezes my ass cheeks with both hands...very hard. I'm pushing back into her strong hands and moaning. I feel her hot breath on my ass as she kisses it and then gives it a small bite. "Oh!" I squeal as it sends a shiver up my spine and I lift my ass higher, "Please!" asking for another. She chuckles, spanks me playfully and says, "later, girl."

I don't think I've ever been so horny. I mean, I've put several plugs and other toys in me before but this one is special...and it even tingles a little. Almost a burning feeling?