I just turned twenty, was in a relationship for almost two years to a hot older commanding bitch who was ten years my elder. We had great sex but she left me for an older and richer man. I also lost my job at the law firm were we both worked, probably due to her efforts, I was just an office person there. Now I'm out of a job and have to move out from sleeping on her couch soon. So this morning I was alone, drinking, naked and searching the web for work.
I somehow found myself on this peculiar list and saw a job opening for a live/work deal if I would be two gay's guy's 'Gal Friday' the ad said. Pay was great, however there was a catch. They lived a 'clothing optional' lifestyle, so they and I would be working naked.
Here I was now completely naked, sitting on my trench coat when I got into my boss's Silver Tesla. He then took me for a 'taste test' which in case you're wondering meant he gave me a blow job!
Oh my God it was the best frigging cock sucking experience I ever had. I'm now waking up from that bliss and recalling how I got to be sitting naked in his car, at noon in front of my apartment.
"Hello sleeping beauty. You not only look yummy, but you taste it as well," I see his thick pink tongue gather up the last bit of my cum on his lips. "You are definitely a keeper."
We pull away from the building and head off, where? I ask and it is in the City about a half hour from here.
"Reach behind and check out what I picked up, get that white bag with the box in it."
I do as instructed and inside is a shoe box. I open it up and find a pair of platform shoes. The plastic bottom part of the shoe is all fire truck red with maybe six inch heel. They are the 'fuck me' style of shoe, backless and open toed with just a single band of clear plastic across the front. I imagine that it would look like you were standing on this red platform which magically adhered to your feet, since the clear plastic would be invisible. Fondling the shoes makes my dick twitch.
"You like them?"
Do Gay guys dress up? I wonder what he'd look like wearing those. He already seems close to six feet, he'd be a giant in these. "Oh yeah, they are hot. Definitely hooker shoes."
"Good. Glad you approve. They will be your everyday-around-the-house shoes."
What? He wants me to dress up? Those bags in back have more stuff like this? Oh Hell. I'm an idiot!
CD! Cross Dressing. 'Passable CD' refers to me being a passable Cross Dresser! That stuff is for me! Shit! Shit! Shit! All those questions about if I was willing to take on the feminine role! It was all literally true. I'm going to be dressed up like their 'Gal'.
"Scooch your butt over." I comply and my bare butt rest against his clothed hip. "I like working a stick while I drive." With that he begins to fondle my prick as we drive. Oh man it feels good.
"Hey, honestly now," I ask as he slowly works my cock with his strong black hands, "do you really think I could pass as a girl?"
"Oh definitely," David answers. "You gave me your measurements, you have a great shape, and since you are an ass man, you must have realized that you have a real hot ass. You must know that any girl would be jealous of that ass you have."
"Really?"
"Oh yes. On top of that, you have lovely eyes, long natural lashes, and a cute small nose and great lips. You are a natural woman."
"Really?"
"Once we get to our place I can show you, I have some make up and nail polish and you just watch how you transform with a little attention to details. You're flat chested but that is sexy in a nubile young thing like yourself. Now settle back and relax, little one and enjoy it."
I just shut up and try and take it all in. He's not just pulling my leg about all this? Well, hey he is pulling something...my cock...I guess he must be for real, he picked me for this gig. So, far this Gay thing is no big deal. He gives great blow jobs and he knows how to handle a piece of meat. Oh yeah...I can live with this.
We finally get to his place and park in the garage. He does manage to keep me hard and hot without letting me cum. Man he is good.
"Wear your new shoes, try them out, and help me carry these bags inside."
I set the shoes down and step into them. I have a natural balance even when drunk, and so I am able to stand up in them without falling on my face. Wow. I feel so fucking sexy and powerful in them.
I then quickly glance around the garage to make sure we are alone. I forgot I'm completely naked standing here. But I don't really care at the moment. I even don't care that I have a raging stiff one.
I take a few hesitant steps, sort of afraid they'll slip off my feet. But I quickly realize that my toes underneath the band keeps the shoes on my feet, especially this pair of platform heels. Then I figure out that the higher the heel most mean there is a steeper angle that my feet have to be in when wearing them and that insures that they will stay on. I always wondered about that. These are cheap but so fucking slutty. I feel like some hot whore in them.
"Well, what does my little girl think about her new shoes?" David grins as he checks me out.
"They feel great. Sort of natural."
"Good. Now, you might want to put on the coat...but you don't have to, it's up to you," he says with a wicked grin. "Then grab the bags, will take our floors private elevator and up we'll head to the top of the building, that's our floor."
As I wrap the trench coat tightly around my body and tie the belt I spot two hunky guys who looked like they just came off the beach, a blonde and a brunette wearing expansive sandals, cut offs and tee shirts. They wave at David as we all head to the elevator. We walk up to an elevator at the end with a security camera, intercom, and electronic door controls.
David wipes out his electronic key and says, "Boys, I got this," and the elevator door opens and we all step in.
There is only a up and a down button. As the two beach hunks nonchalantly thank David as they step in and just as nonchalantly undo their cut offs and step out of them now it is revealed that they both were going commando.
I try not to stare too hard at the two big pieces of meat dangling on display as they are calmly naked from the waist down. They then take off the tee shirts to get completely naked. Man, oh man they have hot firm bodies with those gym-tits and their nice large nipples.
David leans over and whispers in my ear as the two now naked studs joke about the day so far.
"We share the top floor with a couple who runs the most successful gay porn studio in the country. We both have our servers also located on our floor. They throw great parties."
We arrive at the top and the toy studs walk off the elevator carrying their cut offs and tee shirts as they head down the hall. I just stare at their naked butts as they disappear behind a door. David was enjoying the view as well.
Then, we walk to what must be our office. Once there, David just as nonchalantly sets down his bags and undoes his pants revealing he is wearing a teal thong. He slips that off as well steps out of it and slips out of his brown leather loafers.